I have no clue how to approach men romantically. Please help!

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SomethingKindaCrazy asks:

I’m 23F and I’ve never dated before. I’ve never really bothered with it because my home culture was always to focus on grades and family instead of an active social life. Due to my secondary schooling focus, I have mostly guy friends so I don’t have much problem relating and bantering with them.

But I have no idea how to actually approach guys romantically. I don’t know how to flirt because I’ve never needed to (as a side note, is it necessary to know how to flirt?). I don’t really have any female friends who can teach me to flirt because the female friends I have are just as clueless about dating as I am. Hell, they ask me for advice because I’m the only one they know with experience just talking friendly-like with guys.

As for sex, nope. I’m not asexual and do get sexually attracted to people, but I don’t really want to get involved sexually with anyone unless I know they’ll stick around. I’ve been curious about online dating but there’s even a problem there because I don’t take pictures of myself. I just don’t like being in pictures so by consequence, all my pictures look awkward.

So what should I do? Please help.


Demetrius says:

Lots to unpack here, so as is my wont, I will list what I think you need some help with:

  • Hesitance to approach men romantically
  • You don’t know how to flirt
  • You don’t want to get involved sexually with anyone unless you know they’ll stick around
  • You want to try online dating, but are hesitant to take pictures

That sounds a fair assessment of your issues here, even though you really only focused on the first two. Let’s tackle those first.

Hesitance to approach people romantically and not thinking that you’re good at flirting are two of the biggest problems the average dater faces. Let’s be real here, most people have never successfully approached a stranger that they were attracted to, hit on them, and had that interaction lead to a date.The people who are good at flirting and cold-approaching people are usually either naturals because some people are just naturally charismatic, or they worked on building those skills. Handling rejection, reading body-language to determine attraction, how to start a conversation with a stranger, and so on. If you’re wondering what sort I am, I’m the “work on building those skills” type. And you know what, you should become that type too.

I don’t have enough space in a single blog post to fix these problems, so I’ll try to give you some pointers that can work in the short-term, the rest you’ll have to do on your own. I’d recommend a mix of reading (i.e. “How to Win Friends and Influence People”) and watching tutorials. Your main focus should be on trying to build social skills, not “flirting” or “approaching” skills. You’re probably better at approaching guys then you realize because you’re so comfortable with platonic male friendships, but there’s always more to learn and develop. One of the main things I tell people when they say that they want to get better at flirting, or approaching, is to do a lot of low-stakes practice. Start conversations with strangers you have no romantic interest in. Do it often.  If you can get comfortable talking to people in general, that skill translates into talking to people you find attractive. Constant practice can make things like small-talk, or having an anecdote ready almost reflexive. It’s like building muscle memory, but for social situations. Once you’ve gotten to the point where you think that you could approach and talk to anyone, remember these simple flirting tips.

First, smile. Even if your natural resting facial expression looks aggrieved, try to smile, even if it’s a little forced at first, when talking to someone attractive. Forcing yourself to smile actually makes you happier (according to SCIENCE) and humans mimic the facial expressions of the people they’re looking it (also according to SCIENCE). Next, make sure your body language is inviting. That means facing the front of your torso toward the person you’re talking to, not crossing your arms, not moving yourself away from the person, or hunching your shoulders, or slouching. Third, again stay with me here, maintain eye-contact. When someone is talking to you, look them in the eye. Bill Clinton won the 1992 Presidential Election for a lot of reasons, and one of those reasons is the guy knows how to maintain eye-contact. Politics aside, watch this video of a 1992 debate between Bush and Clinton and pay attention to how they do or do not maintain eye contact. It’s fascinating. Now for some people eye-contact is harder than others, so here’s one other tip: stay engaged. Listen to what they say, respond, and ask probing question, and generally keep them talking, even if it means asking them questions about themselves. People usually love talking about themselves. If you’re doing all those things and you’re still thinking that those aren’t strong enough flirting signs, just be direct. You might be hesitant to do that for a wide variety of reasons, but trust me, sometimes when you’re direct and you’ll get exactly what you want. So don’t be afraid to say “Hey guy, want to go on date sometime?”. Don’t be afraid to shoot your shot just because you’re a woman.

Finally, I do want to address those last two points you made. I understand wanting to have sex with someone who you feel will stick around but trust me on this, that will never be something that you can guarantee 100% of the time. You can work to minimize your risks of dating someone who will hump and dump you, but things happens. You can minimize that risk by only sleeping with someone who you’re in a committed long-term relationship with, or are married to, but they can always pick up sticks and leave just like the left-you-after-sleeping-with-you-on-the-first-date guy. Just something to keep in mind. Oh and the whole hesitance to take pictures thing. Listen, I get it. In some pictures I think I look great, and in other pictures I look like Klaus Kinski. The thing is…you need pictures. Hit up a friend, bribe them and ask them to take dozens of pictures of you. One of those pictures is bound to be good, and who knows, maybe five of them will be good! Or get them professionally done if you can afford it. Whatever the case, may be, you’re imposing a barrier to online dating onto yourself and you can just as easily remove it. I think that online dating can be something you’re doing while you’re working on building your social skills up, and it might even help you build stronger social skills. Flirting through text is great practice for flirting in real life.

All that said, remember that your focus should be on improving your social skills, not on just getting good at chatting up guys.

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

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