top 5 dating tips for men over 40

Rock Your First Date (Leave Her Wanting More!)

If you want to rock your first date and make her want another date with you, be unexpected.

When you stand out from the usual suspects (prospects) she’s dated in the past, you automatically intrigue her and pique her curiosity about you.

So how do you rock your first date and increase your chances of a second, third or fifteen date?

Let’s look at a few simple tips!

Feedback from my own and friend’s dating experiences as well as talking with many women.

Rock Your First Date Tips

Do ask her if it’s okay to order for her!

Obviously, we’re assuming you’re on a typical dinner date.

IF you know her from your social circle or have FaceTimed and know there’s mutual physical attraction, I do recommend the traditional dinner date.

As far as ordering for her, some ladies love this kind of chivalry, but others will find it chauvinistic.

If you met online and actually read her profile and chatted a bit before the date, you might already know if you’re on the same page with this.

If not, and if it’s a big deal(breaker), then filter better next time.

Either way, make sure you ask her if she has any food preferences or allergies.

No one likes a first date in the ER. (Though I do know of a couple that met this way!)

Don’t expect a kiss on the first date.

Even if she likes you, it’s not mandatory protocol to pucker up.

If you’re unsure, ask!


God, I really want to kiss you, Ashley.

Boldness, not arrogance or cockiness, is a reoccurring theme for how to rock your first date!

Depending on her age and values will determine if she expects a kiss (or more) on the first date.

Again, this is for those fine fellas who are looking for a keeper, not a one night deep relationship. 😉

However, if you’re attracted to her and assume she’s even potentially attracted to you…

You must at least let her know you want to kiss her; or if you missed your chance, you need to let her know after the fact you’d wanted to kiss her.


Ugh, I really wanted to kiss you, Ashley

She’ll let you know if you should have! And this will tell you if you should kiss her much earlier in your next date!

No sexual tension = friend zone.

Do give her a warm hug after a first date if you liked her.

But ask first!

With the #metoo movement and the pandemic, the world has changed and any physical contact must be consensual.

If she’s good to go then… No teepee hugs. No granny pats.

Linger a bit if you’re hoping for more.

If she doesn’t pull away, she may be open to a kiss; if it’s not super obvious she wants to swap spit a chaste kiss on the cheek is usually safe.

And if she says no, cuts the hug off short or pulls away then abort mission stat!

The silver lining of The Great Pandemic of 2020 is that it isn’t deemed beta behaviour to ask before advancing physically.

Don’t lead her on if you don’t have a romantic interest or attraction to her!

Bad dog.

Reality land is that unless she looks substantially different than her photos or, if you’ve met before, from what she looked like last time you saw her, you’ll probably be attracted.

Men are more visual than women, believe it or not.

You may discover you’re not interested in a longer term relationship with her but wouldn’t mind a quick fling or friends with benefits situation.

Tell the truth. Trust she can handle it.

If she can’t, red flag and kettle bell buh-bye!

Do text her the night after the first date if you’re interested in seeing her again!

You don’t need to make plans right away!

It’s ok to give her some breathing room — always leave them wanting more — but do text her after.


I had a really great time with you tonight, Ashely. I’d like to see you again. x 🙂

This is a bold move other guys don’t do.

They don’t confidently declare they want her and they don’t put it right out there that they want another date.

You’ll find out if she feels the same and if she was on the fence about you it may sway her your way.

From there, she’ll rethink why she might actually be attracted to you after all.

Let her come to you.

And in the meantime, have a life so that when she does, you’re not overly anxious to nail down the first day she’s available.

Here’s a powerful phrase that make women want more… ready?


I want to see you but that day won’t work for me. How about Thursday?

What’s the Wingmam Motto?

Right! Always leave them wanting more.

And if she isn’t interested and was simply overly polite during the date, she might feel more at ease letting you down via text.

That’s ok. Next!

Never be rude, you’re a gentleman of value.

If you question your value, you need my WakeUP2Luv program. PayPal now accepted!

xo Anna

Oh look, a playlist on texting and online communication! Rock your first date and the follow up strategy.

You’re welcome. Flutter 😉