Dating Advice for a Man Over 50

Dating Advice for a Man Over 50

If you’re single, the dating advice for a man over 50 is a little different than for men under 50.

Most men over 50 have been married or in a long term relationship, but not all.

Stay tuned to the end and I’ll share a couple tips for men over 50 who’ve never been married and don’t have kids.

Typically, men over 50 are in a different stage of life than those in their 20s to 40s, especially in the following areas…

Career / Money

Other than in exceptional circumstances, like a pandemic, men over 50 usually have their career and finances in order.

As in, he’s got a job he can reasonably rely on to provide enough money to keep him out of the poor house.

If you’re a man over 50 and haven’t got this part of your life on track, you need to prioritize getting this area in better standing.

Ex-wife / Kids

Many men over 50 are divorced and have children or step-children that are a part of their lives.

This means many women who men over 50 consider dating also have young or grown children.

You need to decide if you want to date a woman with children and what that might look like, or if you prefer to date women who don’t have children, which limits your options.

Sex Drive

Biology dictates that as men near 50 their testosterone declines in a noticeable way.

This is normal… but not mandatory. 😉

Testosterone is the primary sex hormone, so when it starts to evaporate, you may feel like having less sex but more cuddles.

But if you’re dating a woman with a higher sex drive, you may want to top up your testosterone.

Testosterone also keeps you from being a door mat.

Hint: Women don’t want a man who’s a door mat.

There’s a test you can do without having to go to a clinic that’ll let you know if you want more testosterone. Details here.

Money Money Money

Whether she’s 20-something or 50-something+, women who date men over 50 expect those fellas to have their career and finances on track.

But as a man over 50, especially if you’ve gone through an expensive divorce, you’ll want to make sure the woman you’re considering also has her finances in order.

If there’s not a huge discrepancy in assets and income, she should not only be okay with a pre-nup, but want one to protect herself.

After all, does she really want to risk her own assets and income if you get into debt or make a bad financial decision?

That’s how you sell the prenup! 😉

Dependants and Independence

If you’re single and over 50, some of the women you may consider dating will have children.

Watch: Should You Date a Single Mother?

But if she’s considering dating you, she’ll also expect that you may have kids and/or grandkids in your life, as well.

It’s always best to explicitly discuss how involved each of your respective families will be in your relationship, to avoid disaster later.

Never assume she’s involved with her young or adult children the way you are with yours.

Discuss, don’t assume!


I know a couple who got together in their 60s, after both lost their long time loves to cancer. #cancersucks

The woman had three grown children and grandchildren and had been a foster care provider for over 25 years until she retired.

The man had four grown children with grandchildren and great grandchildren. He was the go-to babysitter.

His new lady was done with babysitting.

They had to compromise on how to handle it, so he reduced his babysitting to weekends and if his lady wasn’t feeling up for little ones, she’d spend a weekend at her own place.

They’ve worked it out so they can be together without resentment.

Key point: Love isn’t enough! You’ve got to discuss and agree on some unromantic practical things.

Key point: If you want to have a mutually satisfying intimate relationship with a woman, you both have to make each other a priority over all others (except dependent children in your care).

If you date a younger woman who doesn’t have kids, there are other considerations. Watch the video on that.


If you’re over 50 and dating someone your own age, your sex drive is more likely to be on the same page: more cuddle time, less hard core.

But again, discuss, don’t assume!

And if you’re dating or wanting to date a younger woman, you may need to top up your testosterone! Details here.

Extra Dating Advice for a Man Over 50

If you went through a nasty divorce, don’t be bitter, be better.

Not every woman is the Nasty Nelly your ex is/was.

But also, don’t fall for the same crap different deal. As in, don’t wind up with another woman who looks different but has all the same crappy qualities your ex had.

WakeUP2Luv walks you through how to figure this out.

If you lost your sweetheart to Heaven Above, my heart goes out to you; that’s the worst.

Take the time you need to heal enough to be of value to a worthy woman, but don’t get stuck in grief.

Watch: Heartbreak and Lost Love.

Ch Ch Changes

Realize by the time you’ve made it 50 or above, you’re going to be pretty set in your ways.

Not every way, but some ways, and that means older women will be, too.

You’ve got to decide what the deal breakers and deal makers are and compromise on the stuff that’s really not that important.

Again, WakeUP2Luv helps you figure this out.

No one is perfect, but there’s a perfect match for you.

Dating Younger Women

A man over 50 who’s dating a woman in her 30s or younger will need to be more direct with her.

She not only expects directness and certainty, but if you don’t bring up expectations, deal makers and deal breakers, amongst other practical matters, you could be in for a world of hurt later.

What Kinda Things, Anna?
  • “I don’t want kids. I’m getting (/had) a vasectomy.”
  • “I look forward to living with a woman again but only if she wants to sign a prenup—you’d want to be protected in case I make bad financial decisions, too, wouldn’t you?” 😉
  • “I love that you’re fit/slim/dress nicely/wear makeup/whatever. That’s not only important to me now, but it will be forever. Promise me you’ll always __… What’s important to you?”

Hint: If she says, “A man who loves her ‘for who she is regardless of her weight/clothes/makeup etc.’” or something similar, you can jokingly say, “I’d still love yah… but I’d miss yah!” 😉

Do not let her manipulate you into indirectly agreeing to something that won’t work for you long term!

Stand firm!

You could say

  • “Look, you probably want a guy who’s always got a job or isn’t broke, right?” (What woman would say ‘no’ to that!)
  • “Great, so I’m attracted to your personality but also your body/style/whatever. I have standards, too. If my standards don’t work for you then maybe we’re not a good fit.”

Said with zero attachment or bitterness, just casual friendly finality.

You’ll find out if she can get on board with your deal breakers and deal makers quicker if you know what they are and explicitly express them! #WakeUP2Luv

Key point: If she’s a bit older, she’ll have had life and relationship experiences that create deal makers and breakers for her, too.

Key point: No matter how old you are or what age she is, never go for potential hoping she’ll change for you.

The younger she is the more likely she will change over time, but it won’t necessarily be in any of the ways you hope for!

Never Married No Kids Over 50

Assuming you’ve got your career, finances and health in order you, my friend, have the luxury of dating women of any legal age with or without kids without having to consider exes or offspring.

You can remain in a playing-the-field stage as long as your heart and other parts desire.

I call this Stage 1: Testing the Flavours, mostly reserved for men in their 20s. (More on this in my next vlog!)

However, you will likely tire of this stage eventually and want to settle down with a keeper.

Watch: She’s a Keeper IF…!

Again, the best advice for a man in his 50s I can give is to know your deal breakers and makers in advance so you don’t get caught off guard when some sultry princess sneaks up and melts your heart (while hardening your other parts). 😉

Key point: Love and sexiness are not enough!

Regardless of your age or prior relationship status, my WakeUP2Luv program will help you avoid emotionally damaged women and painful relationships by showing you how to…

filter, filter, filter…

for the right woman for you!

Dooo it.

xo AJ

200+ Engaging Long Distance Relationship Questions To Keep The Conversation Flowing

Reading Time: 13 minutes

Are you in a long-distance relationship? Did you always feel stuck to start a conversation, especially in text messaging? Well, if that happens to you, don’t feel ashamed about it. We all facing the same problem at some point in our life. That why in today’s article, we will share with you a bundle of long-distance relationship questions that you can use to help the conversation flowing.

In every relationship, it is very important for both of you to learn about each other. So that, asking the right meaningful questions is one of the best ways to make the most of your time apart. Asking the right questions also can help you both stay connected and catch a glimpse into each other’s everyday life.

According to the social psychologist expert, Arthur Aron, a professor of psychology at the State University of New York, who published his result in “The Experimental Generation of Interpersonal Closeness.”

He found that pairs who discussed ‘meaningful questions’ were much more likely to maintain a deep connection than those who were not. So, it quite fair for me to say that the quality of conversations can help you survive the distance and grow as a couple.


Long Distance Relationship Questions For Your Partner

In our previous post, we talked about common long-distance relationship problems. And one of the problems is to avoid spending too much time talking to your partner. The reason is quite simple, you need to have a meaningful conversation.

That said, you don’t need hours per day to have a meaningful conversation with your partner. As long as you know what kind of topic to talk about, your conversation will start flowing naturally.

Full article here: Common Long Distance Relationship Problems That You Need To Avoid

Without wasting any time, let’s go through the list of the questions first. But keep in mind, these questions are just for ideas only. Be flexible and play around with it. Maybe you can start with these first then jump off into other topics.

  1. What is the best gift you received from me?
  2. Which song that you think describes our relationship?
  3. How do you keep yourself active these days?
  4. If we had a chance to date, where did you want to meet?
  5. What shows are you watching lately? Any chance we can watch it together?
  6. Let’s be honest, how do feel about our first date?
  7. If there is no distance between us, what is the first thing you want to do together?
  8. What is the first country do you want to visit together next time?
  9. Have you ever had a dream about me or us?
  10. Describe me in 4 words in 20 seconds.
  11. In your opinion, what is a doable frequency of video call that we should make?
  12. What should we do on a virtual date?
  13. Have you developed a new hobby? What is it?
  14. What is one movie that you find worth-watching?
  15. Did you have any specific thing you want to do the next time we were together?
  16. What was your favorite fairy tale growing up?
  17. Can I ask one question, do you feel loved by me?
  18. What song or songs remind you of me?
  19. What kind of fun things do you want to do together the next time we meet?
  20. Is there a game you did like to play that we haven’t tried before?
  21. What can we do to draw us closer to each other?
  22. Do you remember where we first met?
  23. What is your favorite thing for me to wear?
  24. Any ideas on how to flame up the romance in our life?
  25. Are you interested in virtual dates? What kind of date that we should do?
  26. What is the goofiest knock-knock joke you know?
  27. How can we keep our relationship exciting, any other stuff we can do together with other than talking?
  28. What is the weirdest dream you’ve ever had?
  29. What is the strangest thing you ever did as a child?
  30. If you could meet one person today, living or dead, who would you choose to meet?
  31. What is your favorite part of our long-distance relationship?
  32. Did your family had their own tradition? If yes, what is it?
  33. What is the most interesting place you have ever seen?
  34. Which are you like the most, a seaside vacation or a hillside vacation?
  35. Do you want to go on an adventure trip or relaxation outings?
  36. What is the most exciting journey you ever had?
  37. Did you speak any other languages? How did you learn it?
  38. Who has been your friend for the longest?
  39. Did you always keep in touch with your school and college friends?
  40. Did you break any bones as a kid? What was the story?
  41. Who was your favorite high-school teacher? What makes him/her your favorite?
  42. What is one achievement you worked really hard for in your life?
  43. How did you handle the dentist’s office as a kid?
  44. What lesson are you most thankful your parents taught you as a kid?
  45. How does your family celebrate holidays?
  46. Do you have long-distance friends?
  47. What phone app do you use the most?
  48. Who’re friends of yours do you think I should get to know more?
  49. What is your favorite vacation memory?
  50. Where is one place you want to take me when we meet?
  51. What is the most embarrassing memory you have of yourself?
  52. What was the first thing you bought with your own money?

Learn about their belief, life philosophy, and personality traits

When you share something with your partner, a secret, a dream, or an aspiration, it will strengthen your love connection. This may seem obvious, but most of us failed to do so. We’re not asking our partners about their specific preferences.

Read Next: What to do when he pulls away and how to win him back

However, if we know what our partners like and dislike, we will be a better companion for them. Understanding their perspective will help us having a quality conversation and become a better partner to them.

  1. What is the biggest difference between you now compared to the past?
  2. What challenges are you facing right now?
  3. Who has been inspiring you recently?
  4. Who is someone that you always look up to?
  5. What is a suitable word to describe someone you look up to?
  6. What is the one thing about yourself that you want to overcome?
  7. If you could know more about one thing, what would it be?
  8. What is something you misunderstood as a child and only realized much later was wrong?
  9. If you only had a week left to live, what are the things you want to do?
  10. What is something you always wanted to do as a child but never got to do?
  11. If you could live in any era, which it would be and why?
  12. Do you think this distance has helped us grow individually?
  13. When you need your time alone, what is the best way for me to know about it?
  14. What things did you look forward the most in life?
  15. What is one thing you want to be remembered for?
  16. How do you make your decision? Is it based on logic or emotions?
  17. What is your passion in life?
  18. Would you rather be the best player on a horrible team or the worst player on the best team?
  19. What is one thing you want to change the most about yourself?
  20. Do you consider yourself materialistic?
  21. What is one superpower you would want the most?
  22. What is your personal opinion about astrology and horoscopes?
  23. If you had one chance to go back in time, what would you change or choose differently?
  24. What would you say is your worst trait?
  25. What is something that scares you the most?
  26. Can you name one thing that you know is kind of ridiculous, but you still will argue over it to the death?
  27. Do you consider yourself a spender or a saver?
  28. Are you a mountain person or a beach person?
  29. What your personal view about tattoos? Would you like to get a tattoo?
  30. What is one thing you’ve done that you are most proud of?
  31. If you had a chance, what is one skill you’d like to learn and improve?
  32. What task or activity makes you feel happy?
  33. How do you feel if you need to perform in front of the crowd?
  34. What type of surprises do you love and hate?
  35. Do you cry when you sad? When is the last time you cry?
  36. How did you deal with sadness and disappointment?
  37. What is your morning routine?
  38. Did you ever speak the truth but still got punished?
  39. Have you ever make a promise to someone and then forget about it?
  40. Did you ever lie to someone you loved?
  41. How have your friends influenced who you are now?
  42. How did you positively influence the life of your friends?
  43. What do you want your legacy to be?
  44. Have you ever been betrayed by your best friend?
  45. Do you believe that each of us has our own purpose in this universe?
  46. Do you have trouble trusting people?
  47. If you were to write a book, what genre would it be? And why?
  48. What are your financial goals?
  49. Do you keep a budget? Is it helpful to you?
  50. Where is your favorite coffee shop and why?
  51. What books have greatly impacted your thinking and belief?
  52. Do you care about how many unread emails you have?
  53. How similar are you compared to your parents’ personalities?
  54. What do you wish your parent did differently?
  55. Who do you think knows you better than you know yourself?
  56. Does hosting people make you excited or feeling stressed?
  57. What times of day do you have the most energy?
  58. Do you ever take a personality test? How accurate it is to you?
  59. Do you prefer buying things new or used?
  60. What political topics are you passionate about?
  61. What is your deepest regret?
  62. When do you personally find your sense of purpose?
  63. What type of advice would you give to your younger self?
  64. How do you decide who is worthy of your trust?
  65. If you’re a millionaire, what type of charities would you support?
  66. What do you think about hugging and kissing in public?
  67. What is your favorite way to spend time for yourself?


Questions about food choices and general preferences

This section will help you discover what you and your lover have in common. It could be a favorite food, opinion, habit, like, dislike, preferences, and more. Some of the questions will remind them of something they loved and they might share that experience with you.

  1. Are you a coffee or tea person?
  2. What did you eat the most for your breakfast?
  3. Which is your favorite fruit and why?
  4. If you want me to cook for you, what the first thing that flashes in your mind?
  5. What book are you reading now? Any suggestion for me?
  6. Please tell me more about your dream vacation
  7. What is one song or music that always improves your mood?
  8. What type of music that you love?
  9. Should we go food hunting the next time we travel?
  10. What is your all-time favorite childhood present?
  11. What was the coolest gift you ever received?
  12. Did you ever get in trouble in school or college?
  13. If a genie granted you three wishes, what would you wish for?
  14. What is the worst movie you have ever seen?
  15. What food do you wish you cook better than everyone else?
  16. Which sports team would you rename, and what would be that name?
  17. Which game show do you think you can definitely win?
  18. What is something that you thought you’d hate but actually ended up liking?
  19. Can you describe your ideal vacation?
  20. What type of advertisement is super irritating for you?
  21. Do you have a favorite flower or plant?
  22. What kind of pet that you love to have?
  23. What are your three favorite colors?
  24. Pizza or burger or ‘me,’ which one is your favorite?
  25. What type of beverages do you drink the most?
  26. Which household chores do you love the most?
  27. What is the most dominant color in your closet and why?
  28. Do you like spicy food?
  29. Any food that makes you particularly sick?
  30. Which vegetable do you dislike the most?
  31. Do you set the alarm or you can wake up without it?
  32. Do you tend to oversleep?
  33. How skilled are you at cooking?
  34. Did you mind if your partner can’t cook?
  35. Do you love reading the news?
  36. Did you ever cut your own hair?
  37. What chores did you love and hate?
  38. Is there anything you regret the most purchasing?
  39. What is the weirdest thing you’ve ordered on Amazon?
  40. Did you ever get lost in the big market?
  41. What is your biggest cooking failure?
  42. How skilled are you at keeping plants or animals alive?
  43. Did you pray for your family?
  44. Are small or large groups more life-giving to you?
  45. What comforting you when you are sick?
  46. Who always makes you laugh?
  47. What is your role between your siblings?
  48. Do you enjoy making new friends?
  49. What are five simple things that bring you joy?
  50. What did you do when you are sad?
  51. How do you usually hear about the latest news?
  52. Do you enjoy spending time with kids and the elderly?
  53. What things are you tired of hearing about?

What you should ask about their work and career

Some of these questions might be sensitive, but it is also will help you both to plan your future together. Asking about career and work is all about your plan ahead. You want to know how your life together would look like.

Read Next: What to text a guy to make him want you

Having a better understanding of each other career and future plans will help you get a clear idea of what to expect down the road. As an example, maybe your partner’s dream company is near to your place or vice versa. This information will help you progressively plan your career and your relationship together.

  1. How confident do you feel in your choice of career?
  2. What do you think about business? Do you intend to start your own business?
  3. Do you have a backup career option?
  4. What was your dream job when you were a kid?
  5. How did you decide to pursue your career?
  6. Did your current career is the same as the one that you always dream of?
  7. Do you think you had the best job in the world?
  8. Did your career is something worth fighting for?
  9. Will you choose love over your career?
  10. If you feel stress with your job, what will you do to reduce the stress?
  11. What do you hope to achieve by your age of 50?
  12. Is there anything you want to change about your career now?
  13. What is your biggest career-related fear?
  14. If your boss asks for your help with something that not related to your work, how did you respond?
  15. How do you travel to work?
  16. Do you love to work as a team or you consider yourself a solo-worker?
  17. What is the biggest mistake you’ve made as a worker? Did you learn anything from it?
  18. Would you become an astronaut if you had the chance?
  19. In your opinion, what is the most dangerous job in the world?
  20. Would you ever work for a nonprofit organization?
  21. What part of your job are you most passionate about?
  22. If you could start a nonprofit, what would you focus on?
  23. What does your dream job look like?
  24. Would you do anything to get your dream job?


Some deep questions for your long distance relationship

Do not strictly stick to the question that has been listed here. You can change the question and play around with the topics depending on the situation. This section will help you to know if you guys are going in the right direction.

Read next: Lack of communication in a relationship and how to improve it

You can ask their opinion about things here and be open with their answers. Because sometimes, you might think that everything is going fine but actually not for them. So try to ask some questions that can lead to the conversation. Remember, good communication is the key!

  1. What did I do that made you feel most loved?
  2. Just curious, have you ever been jealous in our relationship?
  3. What were your thoughts for the first few months of our long-distance relationship?
  4. What is the one thing that you regret most in your life?
  5. If you don’t mind, what is the most valuable lesson you learned from your past relationships?
  6. What about me that you loved most?
  7. What was one thing you wish I know, but you never had the chance to tell me?
  8. From your perspective, what is the greatest strength of our relationship?
  9. What would you think is our greatest weakness as a couple?
  10. Let’s be open, what is the thing that annoys you the most about me?
  11. Did your family know about us and support our relationship?
  12. Do you feel loved when you with me?
  13. What are the things that you dislike the most about our long-distance relationship?
  14. Do you think we communicate well? If not, how can we fix them?
  15. Do you ever feel like being in a long-distance relationship holds you back?
  16. What is your favorite memory of us?
  17. Do you see us together in your future?
  18. Would you ever consider moving in with me in the near future?
  19. What is one thing you are too scared to tell me?
  20. Is there anything making you unhappy in our relationship? If yes, how can we address it?
  21. Which part do you think our biggest area of conflict might be?
  22. What should we focus on to make sure our relationship stays strong and healthy?
  23. Where will we be in this relationship five years from now?
  24. How can we keep the romance alive in a long-distance relationship?
  25. Are you happy with our current level of emotional intimacy?
  26. Do you ever get jealous in our relationship? If yes, can you share some situations that spark jealousy?
  27. Do you remember the first words I said to you?
  28. Did you ever regret being involved in this long-distance relationship?
  29. Are you ever afraid that your partner may cheat on you?
  30. Do you believe we trust each other more than we did before?
  31. How do you describe me to other people?
  32. From your perspective, how are our personalities complement one another?
  33. What is something I’ve done for you that you are grateful for?
  34. How important is time for yourself within our relationship?
  35. What is one thing about the long-distance relationship that scares you?
  36. What are some things we can work for to create a future together?
  37. How can we better communicate this year?
  38. When do you want to close the distance?
  39. Do you ever regret getting into a long-distance relationship?
  40. Are you ever afraid that I might be cheating on you?
  41. Did you have doubts when we first started long-distance?
  42. What three pieces of advice would you tell someone about long-distance relationships?
  43. Do you believe that everything happens for a reason, or do we just find reasons after things happen?
  44. Is there anything you would like to change about us as a couple?
  45. Do you think that there is a special reason why we met?
  46. When you saw me for the first time, what was the first thing that comes to your mind?
  47. What is the best compliment you’ve ever received from me?
  48. If I drastically changed how I look, would you still be able to accept me?
  49. When you are alone, do you ever imagine that I’m there next to you?
  50. What is one thing you are really dying to do with me?

Practice with a long distance text conversation

Having good communication with your partner is a soft skill. It means that you need to try and practice. But, if you just started having a conversation with your crush, you might not even know where to start. So I suggest you check my article here: What to text a guy you like.

That post might help you get a clear idea of how to start a text conversation with a man you like. Other things that will be cover including how to send the right signal, how to open up a conversation, how to let them know that they are on your mind, and how to keep them interested in you.

If you still didn’t read the post, I highly recommend you to check that post right away.

But, if you have been dating for a while, then these questions are a great way to continue learning about each other. It is also can help you develop good communication habits with your partner. Slowly, you will get into a pattern of how to give and receive love.

Okay, that’s all from me. I hope you learn something from this post and please bookmark this page for your future question references. If you had anything on your mind, please leave your comment below. I would love to hear your opinion.

20 Types of Toxic Low Value Women

Toxic Low Value Women to Avoid Dating or Marrying

These are the types of toxic low value women to avoid dating or marrying!

Casual flings may be ok, if that’s where you’re at, but be wary as these red flags can make her not worth the effort!

Types of Women to Avoid

  1. Bar stars #THOT
    • That hoe over there.
    • Bad habits (like bad boys)!
  2. IG models #FilterMuch
    • They never look like that in real life…
    • …but they’ll try to!
  3. Broke AF #NoDoughHoe
    • You’ll be her wallet.
    • She’ll run your wallet dry.
  4. Jealous #craycray
    • Will never trust you.
    • Even if you deserve her trust!
  5. Clingy Chloe #Needy
    • You’ll lose your autonomy.
    • If she matures, she’ll probably leave you.

If these haven’t scared you away, here’s a few more…

5 More

  1. Gossip Girl #ShitTalk
    • If she’s trash talking them she’ll trash talk you.
    • Now maybe, later definitely.
  2. Boy Toys #Tomgirl
    • Constantly surrounded by beta male orbiters.
    • Why she no have healthy female relationships??
  3. Master Minds #SmartyPants
    • She’s smarter than you.
    • At least, she’ll always think so.
  4. Feminists #ManH8r
    • Thinks men are the enemy.
    • Will never admit feminism has created the divide.
  5. Health issues #real or #Memorex
    • If real, she’ll be limited.
    • If fake, she’ll be unlimited work.

What’s that? You’re a sucker for punishment? Well, alright…

5 More!

  1. Baby Daddy No.3 #YouNext?
    • Makes poor choices by accident.
    • Made them on purpose. Oy.
  2. Daddy issues #trustissues #impossiblestandards
    • Can’t trust you. Or…
    • You’ll never measure up to pop.
  3. Mommy issues #norolemodel
    • Inherited a bad attitude toward fellas. Or…
    • She’s a package deal.
  4. Drama Queen #ActsLikeAPrincess
    • Needs chaos to feel stimulated.
    • Will create it with you if lacking elsewhere.
  5. Princess on a Pedestal #overdone #shallow
    • Relies on her looks to get what she wants.
    • Takes for fricken ever to get ready for an-y-thing!

Here’s the last lap! Exhausted yet?

5 More + a bonus 😉

  1. High maintenance #NeverGoodEnough
    • You can never please her.
    • Can. never. please. her!
  2. Social Media Addict #AttentionHoe
    • Her life is online.
    • Therefore, so is yours.
  3. Politically correct #snowflake
    • Overly sensitive to everyone’s plight…
    • Except yours.
  4. Insecure interrogator #SpyMuch
    • Bad past experiences lead to…
    • More bad experiences she’ll make you part of.
  5. High/Low #BPD

Bonus: Narcissists! #Nasty

So yes, definitely avoid these women if you want to maintain your mental, emotional and financial health!

There are more details in the video, so watch the quick run down with bonus tips!

When it comes to avoiding toxic low value women, filter filter filter, my friend.

xo AJ

Once (or Twice) Bitten?

If you’ve dated (or God forbid, married) any of the women in this list, I strongly suggest watching these videos…


Red Flags:
Educated Women:
High Maintenance vs High Standard Women:
Bipolar vs BPD:
Damaged Women/Narcissists playlist:
Nice Guy playlist:

WakeUP2Luv “GET” WOMEN! (“Life changing!” IF you do the homework!)
Donations & Anna’s Memoir🙏:

Compliment Girls Without Being Creepy!

How to Compliment Girls Without Being Creepy

How to compliment a beautiful woman starts with knowing how to compliment girls without being creepy.

Women don’t like creepy.

Bad boys? Sometimes sure, women like ’em bad, but creepy? No way. Neverrr.

Compliments are not only a great segway to flirting, which I’ll get into later, but also if compliments are delivered with skill they’ll make her feel good.

And she will associate feeling good with being around you. Win win.

But there are different strategies for different settings, how well you know her and how hot she is—or isn’t.

In this blog and video, you’ll learn how to compliment girls without being creepy in different settings; whether you know her or don’t know her; and whether she’s hot or not.

Plus, you’ll learn how to turn an innocent compliment into flirting!

And if you’re curious, I’ll share what my own personal favourite (and least favourite) compliments.

Let’s get into it…

How to Compliment Girls Without Being Creepy

1. Situational

There’s a big difference in what type of compliment to give a girl if she’s in a book store vs a nightclub.

Generally, if she’s not in a nightclub, you’ll want to veer away from physical compliments that can be construed as sexual. More on this shortly.

Whether she’s in a book store, grocery store, on the street, on the tram, at a nightclub or anywhere else, you can safely compliment girls without being creepy if you think about what her intention is for where she’s at.

And, what her intention is or could be for what she’s wearing.

You’ll understand what I mean as we go along.

2. Hot vs Not

Attractive women get a lot of compliments on their looks. Ugly chicks don’t.

Yah, yah, we’re all perfect in the eyes of God, but Reality Land is you and I aren’t the Big Cahoona.

We’re biological creatures with certain tendencies, preferences and influences.

The Hot or Not Rule of Thumb for how to compliment girls without being creepy is to compliment attractive women on their personality and less attractive women on their physicality.

More on this coming up!

3. Do You Know Her?

Does the rule of thumb change if you know her?

If you’ve never met before and you’re either cold approaching or happen to be standing near enough to talk to her, like waiting around for the barista to make your coffees, you’ll want to go with the Hot or Not Rule of Thumb.

If you know her and know she’s fond of you generally, even if you’re in the friend zone, you can test the waters on more physical based compliments.


Never outright compliment the T&A (yep, tits & ass) zones unless and until… (I’ll give you the “unless and until” later if you stick with me.)

4. Be Sincere

Women can always tell if you’re complimenting her to get something from her. If your compliment isn’t genuine it will come off as manipulative and creepy.

Choose something specific you really do like about her to compliment her on.

Here are some appearance based compliments:

If you don’t know her, you might say, “I don’t know you but I know that colour looks amazing on you and really makes your eyes sparkle.”

If you know her, you might say, “I’ve known you for awhile but I have to tell you that new dress is really flattering on you. You look great.”

If she’s your girlfriend or wife, say something like, “Babe, you look beautiful every day but you look extra beautiful today. I really like that colour on you.”

We’ll get into non-physical examples soon, I totally promise.

5. Be Original

If there’s something obvious about her that’s attractive, whether she’s hot or not, she’ll be used to hearing about it.

Find something unique to compliment her on.

It could be about something she’s proud of that you “admire” or “respect.”

“Wow, Ashley, I admire your dedication to the project. Respect the way you must’ve put in the extra hours to get X finished.”

“Chloe, I admire that you don’t follow trends but have great style. Respect.”

Who doesn’t appreciate respect and admiration?!

6. Redirect

If you’re meeting a girl for the first time or don’t know her well, you’ll want to redirect the conversation right after making the compliment and getting her response, whether positive or less so, to avoid awkwardness.

If she’s completely rude, abort mission entirely.

Using the last coffee shop example…

If she says thank you or something neutral (but nothing negative or angry), you can follow up with:

“I should try something different but I always get the same thing. What about you, is there a drink named after you or do you like to switch it up?”


“I’m going to grab a coffee, do you want one?” — or “…will you join me?”

If she’s already your woman you can say,

“Did you do/say/wear that just for me today?” And add a mischievous grin and/or wink.

You’re welcome!

Make sure to stick around because you still want to know when to compliment her T&A without being creepy.

But first, let’s look at #7.

7. Her Smile or Laugh

If you can get her to smile or laugh, or see her smiling and laughing, compliment her on her smile or laugh. (Not both, that’s too much.)

This is one of three physical compliments that is pretty much safe to share with any woman.

The other two safe zones for physical features to compliment are her eyes (windows to the soul) and hair (feminine but not overly sexualized).

Along the lines of smiling is…

8. Laughing

If she makes you laugh, regardless of how well you know her, how hot she is or where you are situationally, tell her she’s funny or witty.

You could say, “You’re funny. I like that in a woman.”

When you tell a woman she’s funny, you’re actually complimenting her on the way she thinks—her brain.

Most guys don’t compliment her sense of humour so it’s original and, bonus, she’ll want to make you laugh more.

Side note: Laughing is contagious and releases oxytocin, which is the same hormone that’s released when you… Oooooooh Myyyy G… #Orgasm

She will associate that good feeling to being with you.

However, this next compliment strategy will turn her off!

9. Manipulation

If you only use canned compliments to get something from her—like sex—she’ll feel that and it won’t feel good.

And she will associate those bad feelings with being around you.

Just before I share with you when to compliment her bits and parts, and along the lines of bad compliments, let’s talk about backhanded compliments.

This tip is contrary to what some of the pickup community teaches…

10. Backhanded Quips

Don’t use a backhanded compliment!

How to compliment girls without being creepy definitely means excluding backhanded compliments.

What’s a backhanded compliment?

It’s when you’re seemingly giving a compliment but you’re actually insulting her.

Backhanded compliment, “You look amazing in that dress, are you hoping to get extra attention again today?”

Playful teasing compliment, “ You look amazing in that dress, are you hoping to get extra attention from me today?” Wink.

The former suggests she seeks external validation. #Insecure

The latter suggests she likes you. #Savvy

You get the idea.

And that brings us to the part where you learn how to take a compliment and turn it into flirting.

From Compliment to Flirting

Give her a compliment and if well-received, follow up with the assumption she did it, said it, wore it—just for you!

Side note: Many of these compliments work slightly modified via text, too, by the way!

Whenever you tease her about potentially having done something just for you, you’re introducing sexual tension in the interaction, which you need to avoid the friend zone.

Now, what we’ve all been waiting for…

T & A

There are three times when it’s not only ok to compliment a woman’s sexual parts, but it’s welcomed.

When you don’t know her but she’s in a situation where she’s dressed to the 9s and flaunting the specific parts you cannot take your eye off.

Example: Night club, photo shoot, in your bed.

Be careful in clubs! Just because she puts it all out there doesn’t mean she wants to be overtly objectified.

Bad example: “That dress makes your t!ts look amazing!”
Better example: “That dress is really flattering, but also really distracting! What did you just say?”

2. She’s asked for your compliment either explicitly or by thrusting her goodies in your face and saying, “What do you think of my dress?”

In which case, you could use either choice in the last example, depending on the vibe and your personalities.

3. You’re in bed together.

Whether it’s your first time or 500th time making whoopee with your woman, always compliment her bits and parts. Be specific.

See Steps of Seduction blog.

Compliments I Loathe or Love


“You’re hot.” #lowbrow

“You’re beautiful.”
“…have great style”
“…like your personality/sense of humour etc”

“I appreciate the info you share.”

“Your coaching has changed my life, here’s how…”

However! I try to give some love to all those who are giving me compliments because I know that they come from a good place in the hearts of good men like you.

Except for the T&A ones! 😉


What Makes You a Real Man to Her? Parts 1-3!

What Makes You a Real Man to Her (Features All Women Love)

What makes you a real man to her? Well, there’s only so much you can do with what God gave you, but there are some features all women love that any man can develop. (3rd video added below!)

And the best part is… the features all women love aren’t physical attributes!

Sure, most women appreciate a man who’s fit and healthy or even nice looking, but if you want to win her heart—and other bits, wink wink—for the duration, you must to appeal to her innate need for what makes a real man.

What Makes You a Real Man

You’ll not be surprised by the first of the features all women love because you hear it over and over again.


This is not to be confused with aggression or arrogance, which are both turnoffs!

True confidence comes with knowing your self-worth as a person but, more specifically confidence as one of the features all women love, is your confidence as a man.

Your certainty in the world with women!

You don’t need to brag or try to impress women and that humbleness translates into confidence.

You’ll see how this plays out as we go through the other qualities of what makes you a real man to her.


You don’t need to be bossy or take over when it’s not your place but you have no problem stepping up and leading.

Women love a man who leads with confidence—ooh la la!

And what makes you a man to her in the area of leadership is when you lead the relationship.

Generally, this comes from being confident in where you stand in the relationship and assuming you’re the best choice for her.

It also comes in trusting yourself to make decisions and then following through on those decisions.

Which brings us to…


Bravery comes from courage.

Courage isn’t the absence of fear, but the presence of fear and the strength to move through it.

Women love heroes!

You can be her hero by making those tough decisions and doing things she thinks are scary.

Whether you’re quitting a lousy job to pursue your career passion or speaking up to your boss about getting that raise you deserve, what makes you a real man to her is your ability to face your fears.

Sure, if it’s something big that could affect both of you—like moving across the country—you may need her support and encouragement, but she’s got to see you making theses choices mostly on your own or she’ll feel like your mommy.

Mommy mode = non arousal mode.

Courage is sexy, but for it to be one of the features all women love, it has to come with self-motivation.

Along the lines of bravery is…

Say “No” (to Her!)

A man who can say “no” to a woman is a man who values himself. Self-respect is sexy AF.

In fact, self-respect is a mandatory pre-requisite to sexual attraction.

A woman can’t be aroused by a man she doesn’t respect. Full stop.

Which means you’re going to need some of this next trait for what makes a real man to her.


Resolve is when you’ve decided something and nothing and no one can get you off track of following through on it.

Worded in another way, it’s the internal strength that allows you to make that tough decision and take actionable steps to accomplish its end.

Like finding another job in that new city before you’ve left your current city and booking the moving truck.

Without encouragement. And without prodding. No hesitation.

It’s you saying, “I got this.” and meaning it for yourself.

Okay, now what about what women don’t love?

It should be no surprise based on the aforementioned features all women love that no women love…Mr. Too Nice Guy!

More details on this in the video.

And, be sure you’re subscribed so you get next week’s follow up with 5 more features all women love and how to be a real man to her!


Speaking of acting like a child… children look to their parents and superiors for validation.

Children don’t know who they are in the world and desperately need authority figures to show them that they’re acceptable human beings.

A real man self-validates.

It means you know who you are and what you stand for and don’t need anyone else’s approval, including your woman’s!

Again, this doesn’t mean you’re inconsiderate. Au contraire!

You simply won’t wither and decay if she dislikes something you’ve said or done—or even if she leaves you. #herloss

Purpose / Passion

One of the ways you can self-validate is by having a greater purpose or passion in life.

Something that drives you to get out of bed every day even when some days are crap.

It cannot be her!

If you put her on a pedestal, she will look down on you.

However, it could be family, which includes her.

Or a career or a mission to save the world or simply working to pay off bills or toward retirement.

And this brings us to…


What makes you a real man to her in the area of independence isn’t about being aloof and distant.

Instead, it’s about not needing her.

You want her, you desire her, you can even adore her! But you do not need her.

Children need their mother.

A real man only needs himself—but is confident and open to share himself with a deserving woman.

When she knows deep down you don’t need her she knows you’re with her because she deserves you—increasing both your value—not because you need her which decreases both your value.

Read that last line again.


Similar to self-validating is the trait of being self-secure.

What I mean by secure in oneself is most easily expressed in the attitude of admiration for those who are better than you in any area as opposed to threatened by them.

So, you’re not jealous—you’re motivated to improve your own situation.

But because you feel inspired, not because you feel lack in any way.

When you can easily and publicly give kudos to the admirable qualities of your competition, you have a high sense of self-security.

Whether you’re looking at career, health/fitness, finance, you trust yourself to do your best and your best on any day is good enough.

This trait often takes time, outward actions and achievements to fully realize.

If you want a customized to-do list on how to achieve this get and do the work in my WakeUP2Luv program and then review it annually!

Is Her Rock

When a man embodies all of the above qualities, a woman can feel fully safe with him and he becomes the rock in her world.

There is no better feeling for a deserving woman or man!

He sees and appreciates her for who she really is, flaws and all and is solid in his own self-worth.

Again, when she knows you haven’t made up unrealistic fantasies about her being perfect, she can trust you really desire her.

You are each others’ biggest fans and encouragers, don’t feel threatened by each other and don’t allow outside forces to negatively influence your bond.

Reminder, we all want the real us to be not only good enough but cherished.

When you know your self worth you express that in automatic and, thus, subtle ways, which enables her to respect you and trust your lead.

Trust and respect are the precursors to amazing love making and a relationship that will stand the test of time.

These are the features all women love and what what makes you a real man to her.If you’ve struggled to understand women, check out my Understand Women playlist and get my WakeUP2Luv program.

xo AJ


No More Mr Nice Guy book:

Single Videos


p.s. Step-by-step road map to becoming the real man your dream woman wants without compromising yourself is here.