“How do I find a boyfriend?”

I’m totally cute. I’m fun. I’ve got at least two brain cells and I use them. I can dance and have a variety of other talents. Unfortunately, I can’t find a boyfriend. I’ve tried everything – hook ups through friends, Match, eHarmony, and even the religiousy sites. (I’m not religious at all) I’ve now resorted to posting absurd ads on Craigslist such as the following: [Insert silly but sincere personal ad that would either be read as hilarious or a little psycho, depending on guy’s sense of humor.] Basically, my Friday nights consist of sitting at home and reading responses from lame-os. So please, tell me….where oh where can I find a social adept, cute, funny, interesting guy with a job and teeth? HELP!

OK, I know this asker a little, but we are not close friends, though I do like her. She is VERY cute, fun, smart, talented, etc., just as she says. So why on earth can’t she find a boyfriend, eh?

Well I know for a fact that finding a date, or a friend, is not that hard. Finding someone who you can consider a date AND and a friend, that’s where it gets tricky. Each added layer is an additional layer of magnitude of difficulty. I’m not the only one who knows this. But I think I’m one of the few that never forget it.

Finding a boyfriend is really tough. For a woman of your quality and standards, it’s going to be even more so.

So first order of business: Give yourself a break. Stop thinking you want to find a boyfriend, and get yourself to a place where you truly just want to meet interesting and attractive men, for the sake of meeting interesting and attractive men, without further expectations.

Second order of business: Leave the apartment! There’s no guarantee you’ll meet anyone decent out there, but it IS guaranteed you won’t meet anyone in your living room.

I’m a big user of the online sites — DUH — but I use them most when my schedule is totally whack and when I’m stuck in the boonies. You live right in town and have a traditional schedule. So no more Friday night online dating!! Log in a couple times a week to be available for real-time chatting, but let the profile do some of the work for you while you are out making yourself available for real-time, real-life chatting. There’s nothing like it for making sure you have chemistry with the guy and that his picture isn’t fake. πŸ˜‰

You live in a big city with a million billion social opportunities. Start shopping.

I know it can feel weird to go out by yourself, but seriously, I’ve found that the reaction to me going out alone is always extremely positive.

Find a bar or coffee house or juice bar where you feel really comfortable. Leave the magazine/book/newspaper at home. You are there to be social. Check out the scene and don’t worry about people realizing you’re checking them out! Make friends with the staff during less busy times. You are charming, so get to charmin’.

Ice-breaker basics: I grab a seat right up front or at the bar. I like to talk scotch with bartenders. Or wine with waiters. Etc. You don’t have to be an expert, just know your taste buds and demonstrate willingness to learn. Be cool and friendly! Once you’ve established a rapport, ask about the patrons, the entertainment opportunities, what are some similar places to visit, what are good parties or promo events to attend, etc.

When you are friendly with staff, it’s easy to show up by yourself, because you’ll know and like people there already.

From there you can check out other patrons, or ask to be introduced, or accept their recommendations for other places. Etc.

Men are incredibly impressed by women confident enough to go out by themselves. Humans tend to travel in packs. I love being a solo agent — there’s no one to answer to.

Striking up a conversation is incredibly easy — the harder part is ending it once you’ve heard enough. πŸ˜‰ Pick anyone you find attractive, casually interview him, trade a number (or not), and move on. Feel free to say you’re there to meet new people, but not looking to hook up right away. The right kind of guy will accept that graciously.

Women are defensive in public social situations. Men are NOT. They left the house expressly to meet women. If they had a woman, they would be home with her. It’s damn nigh impossible for you to ‘rudely interrupt’ a guys’ night out. Groups of guys understand that a cute girl trumps even the longest-standing guy plans. Use this to your advantage.

That’s a 101 on how to meet fellas. I can go on with more details, if you want, but it’s not necessarily germane here.

You may not have trouble meeting “guys.” You may just want to meet ONE good one. Unfortunately, that can’t be the short-term goal. You have to be social, be open, and be willing to get burned, annoyed, and have your personal space intruded upon. Taking those risks and enduring those inconveniences are what makes finding the right one so great! But that might take time, even if you radically change your method.

I personally am in a zone where I like dating and am not looking for a deep connection. But I recognize a lot of people just want one special person to spend time with. I’ve had boyfriends, by the way, and they were very special men and really stood out from the crowd. You see pretty quickly when you want to learn more about someone. But first you have to be out there and open to the idea.

Look, shyness happens. I’m not and it’s really hard for me to understand what it’s like and how it can stop someone from “just getting out there”. So please don’t think I’m being insensitive when I say JUST GET OUT THERE. It’s hard for me to simultaneously sympathize with complaints about loneliness and fear of being the initiator of social contact. IMO, you kind of have to pick one.

I meet men — lame-os and non-lame-os alike — pretty much whenever I want. Most come to nothing, which is fine. Look, I know I’m not the cutest girl . My looks are nice enough. But more importantly, I am one of the most confident women in any room. I have the ability to project an energy that makes me fun to chat up. Most importantly, I don’t give off a vibe that the fella in front of me will have to live up to expectations beyond the moment. Invite and reward positive attention, and encourage but don’t demand future interaction. These are the keys.

(I also have the ability to make it very clear when a lame-o’s attention is unwelcome, and I try to do it without making him FEEL like the lame-o he is. That’s a trickier skill, of course. But when in doubt, get rid of the time-wasting jerkoff and creeps by any means necessary.)

Holy moley, this answer was long. But I feel that “meeting boys” is one of the things I can do extremely well, and it’s so obvious to me, that I really want to help anyone who doesn’t find it easy. I am also the first to admit that OTOH, boyfriends are not my forte’. So I hope you find some of this helpful and applicable in your search.


About amywinns

Semi-snarky, semi-sincere, occasionally ranting, always paying attention. Feminist who can work a skirt and crack a joke. Grammar nerd who is also fun at parties. Mid-career writer/editor with 15 years’ experience in newspapers & magazines who now helps developers at a major media corporation communicate with the suits who write the checks. Pro-women, pro-family, pro-choice, pro-workingclass, pro-entrepreneur, pro-farmer. Like every other bourgeois Brooklynite, I choose local/organic/raw food β€” mostly vegetables β€” whenever possible/reasonable/affordable but I’m not a smug asshole about it. Hometown: Atlanta. Weird hobby: lindy hop. No pets, no kids, no thanks.
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