Late to the (dating) party...and completely clueless

[daggah]

Cliff notes first: I'm a 25 year old guy, not bad looking, not fat, but never got into the dating scene and don't have single friends to go "out on the prowl" with. It's been years since the last time I was seeing anyone and I need help to break out of the loser cycle. I don't date because I don't ask women out, so it's not an issue of always getting rejected. I feel completely clueless about how to get started though. I have questions about things like, is it ok to go to bars alone? Is it okay to just randomly approach women when I'm out like, say, in the store?

 

So that's the short version. Here's my story.

 

I'm about to turn 26 in a week and a half, and I haven't even started getting into the dating scene. The last relationship I was in was back in high school. My problem is that I'll see a woman I think is attractive and I'll say to myself, "wow, she's cute" and then, that'll be the end of it. I've gotten a handful of phone numbers over the last couple of years (as a matter of fact, when I think on it, I've had a decent success rate, most of the girls I've asked have given me their number - even if it didn't go anywhere.) But I don't really have any single friends to go out to bars with or anything like that, so I feel like I'm on my own...it's an intimidating position to be in. I'm basically very introverted, spend a lot of time by myself, etc. I'm a bit of a nerd. I'm not bad looking but the weight of knowing that I'm almost 26 years old and I'm still a virgin and haven't been in a relationship in years tends to weigh heavily on my self esteem. I think if I can get the ball rolling so to speak I'll be OK...if I can have just a little success it'll help build up my confidence and improve my chances.

 

Part of my problem, I think, is my standards. Yeah, I just said I'm a virgin, and I view that as a bad thing because I feel like I shouldn't be (I had my chance with that girl back in high school, hell, I was the one who told her we should "take it slow" - sigh...) but at the same time the desire for sex is not what drives me. I just want companionship. My greatest memory of that relationship and her was not the make out sessions or anything like that, but of a lazy sunday afternoon cuddled up with her on a porch swing. She fell asleep in my arms and I felt...at peace. Like everything was right with the world. But I'm getting distracted here. Anyway, my standards. One problem is that I'm looking for a relationship, not a one night stand. So I feel like bars are not the place for me to go...I'm not looking to hook up. I was actually flirting with this one girl on Christmas Eve and it felt like it was going pretty well, but then she wouldn't give me her number. I'm pretty sure it was because she was there to hook up with someone. Hell I even danced (badly) to country music with her, so I feel like I at least earned a number.

 

So, one thing I'm confused about is, what are the rules, exactly? I know I said I don't feel like the bar scene is right for me but if I want to give it a shot, is it "OK" to go to a bar by myself? Or is that just lame? If I'm out doing normal daily routine things, can I approach a complete stranger to spark up a conversation and try to get a number? I've always wondered if that would be really rude, creepy, or strange.

 

Basically, what should I do to meet people? Where should I go?

 

I've tried the online thing a couple of times. Posted and responded to a handful of Craigslist ads (bad idea), tried to meet some girls on myspace (don't have a myspace account any more), almost even tried eHarmony, but I'm skeptical about spending money on an online dating service.

 

Does anyone have any advice?

[daggah]

Did I post in the wrong section?

[JohnnyBlaze]

No, you didn't post in the wrong section, but you're asking very open and subjective questions. The answer to the easy question is "there aren't any rules". The others get tougher. If you approach a girl in a bar, even if you showed up with friends, you'll probably approach her alone. Otherwise, you risk having your friend steal her out from under you (and yes, it does happen).

 

Note: if you do go to a bar alone, be careful. Without someone you know to talk with, there's a very good chance you'll wind up drinking more, which won't help you achieve your goal here. Not saying you can't drink, but keep your wits about you.

 

I wouldn't worry about the virginity part. It's highly unlikely that any girl you've just met is going to ask, and if she does, she's probably not the type of girl you're looking for, from the sounds of things.

 

As to what's acceptable and what isn't, that really depends on two things; your comfort level and hers. Unfortunately, since we (and you) don't know who "her" is yet, you can only really go on your own comfort level. I've seen guys get numbers from girls walking out of church, and I've seen girls get creeped out by guys in a meet market.

 

I find that many times, you have to time your shot in order to stand out from the crowd. Example: you see some cute girl at a bar on a Friday night. She's surrounded by her friends and half the guys in the bar already - not a good time. To her, you're just one of the guys in line. Next Wednesday, you see her in some local pub playing pool with her girl friend...badly. You, on the other hand, can ride the rails like freakin' subway train. That's the time to step in. You get a reason to talk to her as well as make close contact. After all, what's better; offering to take the shot for her, or standing right behind her, pressed up against her, showing her how to shoot better? One is a momentary comment, one offers physical contact (without making you look creepy).

 

I'm not saying that bars are the only situation to apply it. If you're in a book store and you see some girl looking at a book you've read, you can make some comment on it (either positive or negative). Alternately, find a hook. What makes you stand out in a crowd? Are you funny? Cool (either James Dean or Frank Sinatra)? There's always a way to play on your edge. You just have to figure out when to do it, and what audience to do it to. Unfortunately, that takes time and experience (and yes, a lot of failures on the way).

 

Kinda sucks that, in order to build up your confidence, you'll need to take some kicks to the teeth, huh?

[citizen67]

If you see a woman in every day life and think "wow, she's cute/hot/adorable/captivating [you get my drift]" you should catch her eye and say something along the lines of "I hope you don't mind me mentioning it, but Wow, you ARE cute" and then smile as genuinely as possible (girls can detect the fakes ones) . Any women who reacts negatively to this is not someone you want to know any time soon. It won't necessarily get you a date but it gives you a much better shot than just thinking "wow she IS cute" and looking away when she glances in your direction . . .

[LovieDove24]

Try match.com or some other dating websites. Even if none of the relationships get too far it is definitely a confidence booster. You can see all the people who "check you out" and you can set up several dates this way without having to sleazily approach a girl in a bar.