flirting frustration

Reader D. C. S. writes:

lonely heart

Image: m_bartosch / FreeDigitalPhotos.net

I’m recently single, after a very long relationship, and the last time I was actively flirting with women was about four and a half years ago. So I’m out of practice. I have also learned that I am socially awkward in the hitting on women department. Things go great for most of the interaction, eye contact, laughing at jokes, etc. But, when I give them my number, I don’t hear anything back for days or even at all. Plus, when I hear back it fails completely. She responds, there’s some minor flirting and suddenly, texts stop. Then I find myself frustrated getting absolutely no response. I really can’t tell if it’s something I’ve said or just reading too much into it. Are there some basic rules, tricks or advice I should know, to continue to garner interest from a woman, or things I should do that would help practice and hone these skills?

Dear D.C.S.:

Welcome to the world of single life! It’s a magical place, especially in our later 20s and early 30s, where the scene is full of jaded folks who thought they’d found “the one” but found after several years that they were gravely mistaken and are now left trying to figure out how to mingle with a bunch of other people still holding on to their own baggage.


While I am, of course, writing tongue-in-cheek, I am also trying to point out that you’re not the only one who’s having an awkward time navigating the waters of singlehood-after-long-term-relationship. Most folks our age have been left stunned by the fact that the person they thought they chose for life isn’t actually the person they ended up settling down with. We’ve all kind of lost that giddy sparkle about meeting people that we had in college. We’ve been around the block. Some of us are divorced. Some of us have children. Things are a bit weirder and more serious and oftentimes, a lot more disappointing than they used to be. Keep in mind that the women you’re probably dating feel the same way you do: frustrated, lost, and like maybe this isn’t worth it.

I’m not saying you’re not worth it. And that’s not what the girls are saying, either. It’s just that dating is harder as we get older. We’ve seen a lot more. We’ve felt a lot more. Some of us (like myself) are holding out for that teenage feeling, and that comes less and less often as we get further away from our teens. It still happens, so don’t sell yourself short. If a girl’s not madly in love with you, it’s probably because she’s still freaking out about how she’ll never feel the same way she did when she was 16. Or she’s still hurting from the last guy. I can’t tell you why someone doesn’t call someone else back. And you shouldn’t fret about it either. Let her go.

So here’s my bullet list of advice on flirting in our modern era:

Quit caring. The number one suggestion I can give you to keep the flirting fresh is to quit caring as much as you do. You’re right, you probably are reading into things too much. One major problem about dating at our age is that it feels like the stakes are higher. Our couple-based culture has burned onto our brains that we need to be married and happy by 30 or LIFE IS OVER. This is not true, obviously. We all know many a 30-year-old who is not only single, but enjoying herself. Even some of our 40-year-old friends haven’t ended their lives because they’re not settled down. But the pressure is definitely on, especially for the ladies. The more you can do to make a girl feel like there’s no pressure, the more she will like you, even if she wants to have babies, like, tomorrow. It’s one of those weird psychological tricks, but it works every time: the less responsive a guy is to me, the more drawn I am to pestering him.

Not that you have to get all Pick Up Artist on a girl, but just treat the dating scene like you could take it or leave it. Be so fully immersed in having a wonderful life outside of flirting that it doesn’t matter if a girl calls you back or not. Be warm and inviting, but have such a rich circle of friends that more intimate relationships can just be the cherry on a delicious, already-frosted cake. If she doesn’t text you back, delete her number and move on.

Be funny. In spite of all the douchebaggery surrounding his comments that women aren’t funny (obviously he’s wrong — I’m hilarious!), I do agree with Christopher Hitchens to some degree: “The chief task in life that a man has to perform is that of impressing the opposite sex, and Mother Nature (as we laughingly call her) is not so kind to men. In fact, she equips many fellows with very little armament for the struggle. An average man has just one, outside chance: he had better be able to make the lady laugh.” (Vanity Fair, January 2007) While you may be extremely physically attractive, that’s not going to cut it for a girl. We’re not as into the physical side as you guys are, at least most of the time. Find a comfortable humor that works for you and just make her laugh. If you can’t make her laugh, maybe she’s the wrong girl anyway.

Avoid the self-deprecation. The only time self-deprecation works is when you are so hot the rest of us are ashamed of ourselves and we couldn’t possibly believe there’s anything bad about you. If Brad Pitt says, “Oh, you know, my penis is small,” we laugh it off and continue fawning all over him. If Joe Normal says it, we believe him. Not only do we believe him, we think he has a complex about it, which is even worse than actually having a small penis. So keep the self-deprecation to moments when humility is really necessary.

– On that note, be confident. Know what you’re good at, know that you smell good, know that you’re well-loved and wanted, and we’ll feel the same way. But the confidence extends beyond just what you’re good at: we also love it when you try something you’ve never tried before, or re-try something you think you’re bad at or didn’t like the first time. Sing that song at karaoke. Play mini golf. Eat escargot. It’s not about bragging about what you’re good at; it’s about not being so wrapped up in your insecurities that you can’t do something new. This will also help with aforementioned “not caring so much”. If you’re amazing and you know it, deep down, it won’t matter if the girl doesn’t call back.

Practice makes perfect. Just think of all these non-returns as practice for the time you really hit things off with a girl. While I know we all say life is not a dress rehearsal, dating kind of can be. Treat the flirting period more lightly than you would a serious relationship, and have fun with it. Don’t take things personally if your flirting doesn’t work out. While there are some things you can probably change to snag the right girl, 98% of the whole process is just mood lighting and chemistry, both of which you have little to no control over. So don’t worry about it. Just enjoy yourself.

If you want more specifics on what to do on a date, check out my post on dating tips for straight guys.

A quick, weird idea: maybe you could ask the girls who don’t respond directly why it is that they don’t respond. It’s kind of like asking an employer why you didn’t get the job, and you have to be tactful in your questioning. Don’t accuse her of anything, and admit that you understand she’s not interested, but you want to know why. If you do go this crazy route, be prepared for her to say something you don’t like and that may hurt your feelings. Keep in mind that you’re obviously not going to date, so you don’t have to take this as personally as you would if your actual significant other laid it out on the table. Don’t get defensive, definitely. But if you can use it as a learning experience, why not? And if you do decide to go this route, let me know, because I would love to hear what responses you get.


3 Responses to “flirting frustration”

  1. 1 Brian
    November 10, 2010 at 12:58 pm

    “But, when I give them my number, I don’t hear anything back for days or even at all.”

    Not to reinforce gender roles or anything, but shouldn’t the man ask for the woman’s number and call HER? If I gave a woman I just met my number, it would be basically the same as giving it to my cat. Be a man.

  2. November 10, 2010 at 1:04 pm

    Nahhhh I think it works either way. A lot of my friends prefer to get the guy’s number so they can have control over the situation. And most of those girls do that trick so that they don’t actually have to communicate with the guy, so be wary. But actually I have given my number to guys who asked for it and still didn’t call, too. If she wants to talk to you and has your number, she’ll call. No need to over-stalk here.

  3. 3 Brian
    November 15, 2010 at 10:40 am

    Your response is very good. My advice would be to date as much as possible. Easiest way to do that is Internet dating. It gives you a lot of practice plus you meet some really cool people that way (horrible people too, but you just move on). I was way out of practice when I got out of my last relationship. By the end, it was a lot easier. I had gone on so many dates there were no nerves. If someone didn’t call back, I didn’t care because I already had a few more lined up. When you meet someone you like and they like you, you will know and then can just focus on them.

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