business man winkingDear Sandy,

I typically do not comment on a woman’s appearance even if I think she’s a knockout. It’s been a policy of mine to avoid making ANY comment along those lines, thinking that women hear stuff like that from guys all the time on first dates and that it might seem like a “line,” or a come-on, or insincere. When I do express my attraction to and appreciation of a woman’s beauty, I want it to be meaningful to her and myself.

So, I don’t know how to show I’m physically attracted to a woman in a sincere, simple way on a first date. I kind of see it in black-and-white terms. Maybe I’m just inept at it. I think my approach is working against me. On a lot of my first dates, we have incredible discussions, but I end up feeling like romance is not in the air, even if do feel attraction and a spark.

How about an article for guys about the appropriate, sincere, simple ways to show a woman we’re physically attracted to her on first dates or other initial points of connection? It seems like decent guys can do it in ways that are awkward for the woman, not well received, inept, off-putting, poorly-worded, etc. that end up being counter-productive.

I need the advice, and I’m sure there are plenty of guys like me. Women would benefit from guys handling this better, and maybe there’d be more successful first dates for everyone as a result.



Dear Jay,

Thank you for this great question. I can totally relate, because I used to be a female version of you. In my teens and twenties, I was the proverbial anti-flirt. I had a lot of male friends but very few boyfriends. I was considered “one of the guys,” engaging in intellectual conversations, kidding around, and playing sports with the boys. In short, I was a lousy flirt.

Like you, I thought flirting was inauthentic, an overtly sexual come-on, and if you put your sexuality out there, you should be willing to accept the outcome. I didn’t want sex on a first or second date, and I wanted to be authentic in my interactions with men. Sound familiar, Jay?

How can you be an authentic flirt?

I now know that flirting doesn’t have to feel fake at all. I like to view flirting as more playful, less sexual. It’s not necessarily an invitation for sex, especially before you know someone well.

It really boils down to self-confidence. When you’re feeling confident, you feel comfortable engaging with just about anyone. You flirt with the cashier, your next-door neighbor, your friend’s baby, the mail carrier. You exude warmth and sexiness, which is very attractive to both sexes.

Learn how to flirt from pickup artists

My suggestion to you, Jay, is to Google “how to pick up women.” Believe it or not, pickup artists can teach you a lot about self-confidence and building up your sex appeal. My 22-year-old son is an introvert and often found himself in the friend zone with women. He learned how to build rapport with a woman by watching some master pickup artists.

While I’m not advocating for you to manipulate women and get all sleazy like some pickup artists, I am suggesting that you learn how to get your “game on.”

So, practice being more playful in your everyday life. Flirt with the cashier at the grocery store. Tell her you like how her earrings sparkle. Smile and say hi to the people you pass on the street.

It may feel inauthentic at first, but over time, it will start to feel natural. If you practice with everyone, you’ll be comfortable on your next date. You’ll start putting out the vibe that you are interested in a woman for more than her smarts.

Compliment her

You said you were uncomfortable giving compliments to women, as they probably hear them all the time. I don’t think there’s a cap on compliments. Most of us don’t hear them enough. Women love hearing compliments, as do men. On a first date, if a man says he likes my smile, or that I look better in person than in my online dating profile, I feel that he’s attracted to me. That makes me feel good. It’s a turn-on.

Show a woman you’re attracted with your body language, your compliments, and your playfulness. Top it off with a goodnight kiss, and you’ll give a clear message that you’re attracted.

Practice, practice, practice, and you’ll soon be going on your LAST FIRST DATE!



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Advice To The Guys: Learn How To Flirt was last modified: by

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