How soon should I ask her out?

Miscellaneous and Personal Stuff I Must Share
101

[QUOTE=Soapbox Monkey]
Today was…good. Surprisingly good. There was no awkwardness between us. She didn’t hesitate to sit down right next to me at lunch, conversation was fine, even…dare I say flirty at times? Which just makes me a bit confused.

Anyway, I guess I’m now officially Jim Halpert.
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That’s called being friendly. Sometimes, when women are simply friendly guys read flirting into it. Don’t give her motivations that she hasn’t expressed, unless the entire tone of your interaction were to change MONTHS in the future. Respect her enough to assume that what she has communicated to you has TRUTH in it. And if what she said was true (she’d date you, but its not a good idea) then there will indeed be an undercurrent of flirting…anf from here you become good enough friends that you and she are willing to risk your employment to see if its deeper.

She is a wise woman to not risk her employment over something that could be four dates and the discovery that you (or she) turns out to be a psycho. I’ve seen that go down at work - it wasn’t pretty.

102

[QUOTE=Dinsdale]
Didn’t Jim eventually get laid? :cool:
[/QUOTE]

Yeah, after about 4 years of soul-crushing anguish over his unrequited feelings for someone who was engaged to be married. I don’t think I’d be up for a thing like that. Tried it in the past. Not doing that again.

Maybe I’m not quite wired properly when it comes to social situations due to my lack of ever experiencing a real relationship, but I don’t just see a cute girl, ask her out and feel indifferent if she says no. I still very much get crushes on girls. But where as in high school I was incapable of even approaching those girls, now I can.

Her rejecting me doesn’t just make my brain go “oh well then, onto the next one.” It’s never that simple for me. It would be really fantastic if she turns out to be a complete bitch, but if I continue to enjoy her company and her personality, my feelings are only going to grow. And if my feelings DO grow, then by asking out any other girl I would just be attempting to get over this one, which isn’t fair to the new girl.

And of course if I do become close friends with this current girl and she starts dating or hooking up with someone…I really can’t think of words to describe how horrible that feels.

Why can’t this just be easy? It seems to be for everyone else.

103

[QUOTE=Soapbox Monkey]
Yeah, after about 4 years of soul-crushing anguish over his unrequited feelings for someone who was engaged to be married. I don’t think I’d be up for a thing like that. Tried it in the past. Not doing that again.

Maybe I’m not quite wired properly when it comes to social situations due to my lack of ever experiencing a real relationship, but I don’t just see a cute girl, ask her out and feel indifferent if she says no. I still very much get crushes on girls. But where as in high school I was incapable of even approaching those girls, now I can.

Her rejecting me doesn’t just make my brain go “oh well then, onto the next one.” It’s never that simple for me. It would be really fantastic if she turns out to be a complete bitch, but if I continue to enjoy her company and her personality, my feelings are only going to grow. And if my feelings DO grow, then by asking out any other girl I would just be attempting to get over this one, which isn’t fair to the new girl.

And of course if I do become close friends with this current girl and she starts dating or hooking up with someone…I really can’t think of words to describe how horrible that feels.

Why can’t this just be easy? It seems to be for everyone else.
[/QUOTE]

Who says it is easy for anyone else? You have a skewed set of expectations here. What you described as your feelings right now, as far as I know, is more or less how everyone feels. I sure know it was how I felt. Did I mention that I was you three years ago? It’s hard and it sucks, but you really do need to hang onto the good things that have come out of this experience.

  1. you make a good first impression with girls who you think are out of your leagure
  2. these types are girls clearly aren’t out of your league so you should spend more time talking to them than you have been.
  3. she said no and you are just fine. Maybe a bit hurt, but really, you’re fine.

You think your feelings for her will grow. Honestly, if you actually meet someone else this one be true. It is unlikely that this chick was your one true love. Just go out and talk to girls.

You asked her out and it didn’t work out. If you are doing it right and are exceedingly charming and charismatic. Just keep at it. I am not going to lie and say it gets easier. People say it does, but I haven’t known this to be true personally. Every rejection was a crushing blow. But it never stops being AWESOME when it does work out either. And the awesome was always way better than the bad. Eventually it became worth the risk.

But to get to that place you need to go out and see for yourself. The more people you meet, the more people you talk to, the more new situations you explore the more chance you have to practice. Think of it as practice. Try not to get invested so soon. If you have a couple of dates and you like the girl then you can let yourself get invested, for now try to take the pressure off yourself and just have a good time and meet some people.

104

[QUOTE=Soapbox Monkey]
Why can’t this just be easy? It seems to be for everyone else.
[/QUOTE]

Dude, it’s difficult for almost anybody. I only know one person who it’s easy for, and that’s because he looks like Brad Pitt. I’ve hung out with the guy and there are girls literally flashing their tits at him.

His track record for long term relationships isn’t stellar, but he is the one person who I’ve met who makes it look easy. And I suspect when girls are throwing themselves on you all the time, it tends to make you fairly confident. You’re young and you’ve got a lot of opportunities ahead of you. Work on your conversational abilities and women love a guy who can make them laugh.

105

So NAF, you said you were me three years ago? How did things turn out for you? I’m so frustrated with being surrounded by couples, forcing myself to laugh when jokes of a sexual nature are made, when sex is spoken about so casually, when aunts ask me for the umpteenth time if I’m dating anyone yet, that I’ll definitely be needing therapy if I’m still single in three years.

Given everything I’m going through right now with my family, therapy is probably something I should have been looking into, but I also don’t have all the free time in the world anymore. Still, I think I’ll look into it.

I mean, it’s probably not healthy that when confronted with the realization that a girl I really like is having sex with somebody, I feel like my intestines are going to rupture.

106

[QUOTE=Soapbox Monkey]
So NAF, you said you were me three years ago? How did things turn out for you? I’m so frustrated with being surrounded by couples, forcing myself to laugh when jokes of a sexual nature are made, when sex is spoken about so casually, when aunts ask me for the umpteenth time if I’m dating anyone yet, that I’ll definitely be needing therapy if I’m still single in three years.

Given everything I’m going through right now with my family, therapy is probably something I should have been looking into, but I also don’t have all the free time in the world anymore. Still, I think I’ll look into it.

I mean, it’s probably not healthy that when confronted with the realization that a girl I really like is having sex with somebody, I feel like my intestines are going to rupture.
[/QUOTE]

I think therapy is an excellent idea. Of course, I believe most people could benefit from therapy for some reason or another.

You might ask the therapist to assist you in understanding why you attach such strong feelings to people that (at least in this case) you don’t really know that well.

107

[QUOTE=Sleeps With Butterflies]
You might ask the therapist to assist you in understanding why you attach such strong feelings to people that (at least in this case) you don’t really know that well.
[/QUOTE]

Well that last bit wasn’t in reference to my current situation.

108

[QUOTE=Soapbox Monkey]
So NAF, you said you were me three years ago? How did things turn out for you?
[/QUOTE]

Nutshell version.

Three years ago I snapped myself out of it the serious funk you are in. I did it by saying “screw this” and actively not trying to date but at the same time trying to spend as much time as I could going out. I actually did the “I will not date” bit four years ago, but for the first year it was a lie. Anyway, I made new friends, got a hobby or two. Two years and change ago I met a nice girl who didn’t think it was fair that I “wasn’t” dating. I am getting married in 10 days.

Turned out ok for me.

109

What you’ve got to do is get rid of the notion of “one true love” and music and angels when you are with your sweetie. Movies, TV, and books have portrayed love as unrealistically wonderful, when usually it’s much more awkward and painful. Finding someone you’re crazy about is exciting, but often that person won’t share your enthusiasm. You just have to tone it down and be cool, not every pretty girl is going to be into you.

And every girl you fall in love with is not going to be your true love. You really don’t want them to be, you really NEED experience at dating and being part of a couple. Feel free to mess up. If you somehow met and married your one true love at 20 years old or whatever your age is, at 35 you’d probably be tired and wondering what you missed out on in your 20’s.

Don’t get overly attached because fear leads to anger and anger leads to the dark side. I mean, don’t put up with a bona-fide girlfriend cheating on you, but you really need to let go and be flexible otherwise. Put forth effort, but be prepared for things to not work out, whether it be a phone call, a date, or the rest of your life.

110

If it helps, I don’t think the anguish of possible rejection ever recedes. However, you do appreciate the feelings of the other party a little more clearly.

However, there is no pressure on you to date, go out with, or spend anytime with anyone if you elect not to. When I was the age I believe you are now, I wish I had of had your considered approach.

111

[QUOTE=control-z]
What you’ve got to do is get rid of the notion of “one true love” and music and angels when you are with your sweetie. Movies, TV, and books have portrayed love as unrealistically wonderful, when usually it’s much more awkward and painful. Finding someone you’re crazy about is exciting, but often that person won’t share your enthusiasm. You just have to tone it down and be cool, not every pretty girl is going to be into you.

And every girl you fall in love with is not going to be your true love. You really don’t want them to be, you really NEED experience at dating and being part of a couple. Feel free to mess up. If you somehow met and married your one true love at 20 years old or whatever your age is, at 35 you’d probably be tired and wondering what you missed out on in your 20’s.

Don’t get overly attached because fear leads to anger and anger leads to the dark side. I mean, don’t put up with a bona-fide girlfriend cheating on you, but you really need to let go and be flexible otherwise. Put forth effort, but be prepared for things to not work out, whether it be a phone call, a date, or the rest of your life.
[/QUOTE]

Ditto the above.

I came back to this thread to clarify my last post because I realized that I made it sound like I never dated finally said “fuck this noise” and met the woman I was going to marry. That isn’t actually what happened. I was in two long term relationships before that and in between them I dated quite a bit. After the second one I was a bit crushed and went through a dry spell which fed into itself as I became increasingly lonely and desperate.

My point was, it wasn’t until I took the pressure off myself to find someone that I was able to find anyone. I actually dated a fair bit durring that “I won’t date” period. I just didn’t go into the dates thinking that was what they were. Most of them didn’t make it to a third date. I did see a girl for about 2 months in that period fairly casually. But I wan’t looking to date, I was looking to just meet people and have a life outside myself while at the same time being happy with myself. It took me about a year of saying that was what I was doing for it to actually be true, and then a year and change of me really doing it before I met someone that made me reconsider the possibiltiy of having a serious relationship.

So take the pressure off yourself. Figure yourself out. Meet new people, focus on making new friends. If something happens it happens, but don’t go into situations expecting to meet someone. Be ok with being alone.

112

I think taking pressure off yourself (and any potential love interests) is a great idea. It is probably one of those “easier said than done” things, though, that Soapbox Monkey won’t be able to do until he’s had more experience and gained some perspective. Nice Catch-22, eh? :smiley:

Honestly, Soapbox, women in general and this woman in particular are not all that special. What is that t-shirt that I saw awhile ago? “No matter how gorgeous a woman is, there’s a guy somewhere who’s tired of her shit.” Something like that. I’m not a believer in the one true love for everyone - I believe in the spectrum of compatibility, and there are many, many women compatible with you on that spectrum (and you won’t work with most of them).

113

To take my mind off of it, I would literally have to remove myself from civilization for an extended period of time. And even if I did that, I would have no one to occupy my time and keep me busy, and so I would spend all my free time in my head, which is a very bad place for me to go. All my Straight Dope threads come out of that place. It’s not a pleasant place.

There’s no escaping this mindset. I spend at least a quarter of my time dwelling on my social failings, and that’s when I am keeping myself busy with other tasks. Sure, I could go around saying “screw it, I don’t care if I don’t meet anyone” but it would be complete bullshit. I’m not saying I go into every social situation expecting to meet someone, but I’m always hoping. And consistently disappointed.

I’m not necessarily looking for my one true love either. I’m just looking for something. Anything. You likely don’t marry the first person you date, but the longer you have to wait for that first date is all the more you have to wait to eventually find the right person. I have entirely too much catching up to do with these people who, for the most part, are a year younger than me. Many lunch conversations amongst our group have steered towards past and current relationships and I just sit there praying no one asks for my perspective. I don’t like lying to people, but I’ll make something up if I have to.

114

Have you checked out any online dating sites? I’ve met a couple of people on them, including my last girlfriend. Just get on there and look for a casual date, even if it’s someone you may not be very compatible with. In fact, that may be best just to get practice in. Once you go on a date or two even if it’s some psycho chick, you’ll feel a lot better about yourself.

115

That’s what I looked at online dating as - speed-dating (you can meet many people in a short time, instead of waiting years for interesting ones to come along). Dating is like anything else - the more you practice, the better you get. The more women you meet, the less likely you are to idolize them as you realize that there are tons of women out there who are interesting and interested in you.