4 Ways to Flirt With a Man…Like a Grownup

Maybe you used to be a great flirt, but how do you flirt with a man now? No matter your age, the way to connect with a man in the “I think you’re hot and would be interested in going out with you” way is still to FLIRT, sister.

When I suggest that to the over-40 single women in my dating workshops and coaching programs, I can see them cringe. Most of these otherwise outgoing women have no idea how to flirt with men, nor do they want to. They consider it quite childish, bordering on classless.

I have news for you: Here is what you get when you don’t flirt with nice men: a nice conversation. That’s it. But you’re not looking for a buddy, right? When you meet a man you’re attracted to you want to be seen as a W-o-m-a-n! You want to be seen as someone he will consider asking out.

Here are four ways to flirt with flair and class…and get that date, and the next:

1. Compliment him.
Have you ever noticed that we use compliments to connect with other women? “I love your purse!” “Your job sounds amazing!” “You crack me up!”

Why don’t you do that with men? Granted, it takes a different approach, but everyone likes to be complimented. Men love to know that you consider them to be smart, capable, fascinating and funny. A sincere compliment in those areas will take you a huge step forward toward connection. (Ahem: note the word “sincere.”)

You can tell him he has nice eyes, and he’ll appreciate it. But that won’t go so far as more substantive compliments. A confident, grownup good guy needs to hear more than you think he’s cute.

Tell him when you agree with something he says; ask his opinion; let him suggest a book or restaurant; laugh at his jokes or tell him his business sounds interesting. Tell him you want to know more about something he’s interested in.

Men rarely receive compliments from women. When you do, you will stand out and he will take a second look.

2. Use your beautiful body.
Using your body to flirt does not have to be slutty or silly. Remember how you flirted when you were 22? Much of what attracted those boys in bars is still what attracts men in Starbucks or in your hiking club. .

You can be be subtle but very clear. Stand straight in front of him, feet parallel with his, and make eye contact. Be playful. Brush your hand against his arm or shoulder, twirl and flip your hair, and use open hand gestures.

Responding to this type of behavior from a woman is instinctive, ladies. Men can’t help themselves. He won’t even know what’s happening to him; he will just know he likes you.

3. Show off, sister.
This may be the hardest part for you; it is for many women. We aren’t used to talking about ourselves because we’ve been told it’s selfish and braggadocios. (Yay! I get to use that word!)

You’ve got to get over this if you want to help men get to know you. He’s only going to know how fabulous and confident you are if you get some of your shiny stuff out. Squeeze in mentions of your passions and interests, accomplishments, interesting life experiences, kind hardheartedness and dreams for the future.

You will get attention and get dates by being memorable and just a bit enticing. Don’t tell him long stories. Keep it brief, and if he’s a match for you, he will want more.

4. Show clear interest.
A simple: “I had a great time” isn’t enough. Everyone says that, and it’s likely to be filed under the “maybe she’s just being polite” category. Instead, add something to that. “I had a great time talking with you, Bob. It would be nice to do it again.” That makes it clear that you’re open.

There’s a big difference between this and asking him out. After you deliver this line, stop! You have helped him feel safe and appreciated. If he’s interested he will make a move.

One last note: Remember that if he doesn’t go for your attempts, he probably knows something you don’t about why you’re not a good match. (He’s married, is obsessed with something you don’t like, is not looking for a nice girl, is mad at women, etc.)

Don’t let it discourage you. You’ll get points in your dating karma bank by making him feel good about himself, and it will be easier to do it the next time with the guy who may be your perfect match.

  1. Hi Bobbi,
    Flirting is something I haven’t done in 50 years. I think I need ti come back to this and reread it every day for awhile. This is going to take some practice.

  2. Peggy, it takes TWO people to make a match. In other words, it needs to be mutual. What you are talking about is a mismatch. In that case, don’t take it personally and move on. – Bp

  3. What happens when you find a match but you are not his match ?

  4. “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” Theodore Roosevelt

  5. Thanks Bobbi, very wise and helpful advice, committing to memory!

  6. You can’t make him want to give. All you can do is to be open to receiving, let him know what you want/need, and Give of yourself. If nothing comes back that’s about him. Find a man who wants to add to your life, not just take. Bp

  7. Tank you Bobbi, the lines sounds familiar. I reflected on some dates that I got and kept for long and agree. I think what stands out for me is not getting a date. But keeping a relationship going. My ex-husband got hooked to e for compliments that I don’t struggle with. He gave them back but then he left the complement thing to me. I got tired because i gave him what he wanted but he did not sustain giving it back. i think my question would be to you, “How do i keep him giving back?”

  8. […] It’s more about remembering how to engage with men from a place of femininity. This will help you break the ice for real flirting down the […]

  9. That was a near-perfect instance for the use of the word “braggadocious”. Presumably, you were looking to use an adjective, but you spelled out the plural noun form by omitting the “u”.

    Proofing helps, but I noticed the spellchecker here marks the adjective as misspelled and offers the plural noun instead.

    This comment is intended as constructive support and not as a pernicious and petty attack on your writing skill or style.

  10. […] killer smile so make sure to please her. It’s that false time disqualification is nonverbal, but my experiences and they see your best face on show her your own phone. I keep improving my life as a person listen to her. What […]

  11. […] second bartender wanted me to do something gets serious, then you gently clasp her hand while you’ll use common […]

  12. Great! I’m so glad and thanks for letting me know Nicola. I love hearing it! Let me know how it goes.

  13. lovely practical and KIND suggestions for how to flirt and communicate with men! Thanks – you have given me a couple of ideas to try out straight away.

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