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FaintestInkling FaintestInkling is offline
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All right, so I’m very soon going to be 27 years old, and I have never had a girlfriend. Not only that but I have never even kissed a girl, and I haven’t had a date or held a girl’s hand in about 7-8 years now.

I’m not trying to tell my life story here, but I know someone will say they need context J, so yeah, this is insanely long.

Basically, I am pretty shy, and I used to be much shyer. I let a pretty bad rejection by a girl I had a huge crush on in high school hold me back for way too long. Then in college, any time I “got to know a girl as a friend” (which I thought was appropriate), she’d have a boyfriend. In law school, I was just too busy to worry about it. If I’d met someone I liked, I would have pursued it, but there simply wasn’t any single girls I ran into to whom I was attracted. I was then extremely busy with work for a year or so … but about a year ago (perhaps not unrelated to my younger brother getting married), I kind of took stock of things and saw most of my friends in long-terms relationships or married, some with kids even, and thought, I have to really do something about this.

I know the line “be happy being single,” but I want to have a family, and I just don’t feel like I can have a full life without ever having a relationship with the opposite sex, despite wanting it. I’ve always been attracted to women, and enjoyed their company, but I also always had a problem “hitting on” them or flirting. It seemed disrespectful, almost.

Another thing that occurs to me is maybe I’m too picky, and I ought to try to go on dates with more women, even if I’m not sure I’m attracted to them … I remember hearing in a psychology class that people “tend to get rejected down to their own level of appearance,” and I find that a rather discouraging thought … I don’t really think I’m *that* shallow, but I can’t stand the thought of telling my wife I think she’s beautiful if I don’t think actually mean it … And I’ve been attracted to some women other men have told me they thought were basically average in appearance. (Didn’t get anywhere, of course.)

So for the last year I’ve been reading advice and asking friends advice, and trying to think of things … I’ve tried to pay more attention to my own appearance … started working out again … Accepted any reasonable social invitation. Let friends who are in relationships know that I’m looking, if they know singles. Try to be confident. Try to be more friendly to just everyone. All that stuff. So far, striking out pretty hard. I still have trouble meeting women I like and who are single. Demographically, there are not many single women close to my age in my area. eHarmony is proving a pretty big disappointment. On since early April, and 168 closed, 16 unresponsive communicating. Only 1 OC that died out over an unnecessarily long period of time, and no phone calls or meets.

Despite all that, I’m trying to stay positive, I figure I’m bound to get a date eventually, and everyone says confidence is so key.

BUT I really have trouble being confident when it feels almost like “it’s already too late.” I should have learned how to do this a long time ago. I know that “needy” and “desperate” is bad, but … I do feel desperate. It’s matter of trying to “hide it.” Surely other people must feel this way, despite all the “live your life” talk? (Not that it’s bad advice, just easier said than done!)

I feel like there is something profoundly wrong with me that somehow any woman I like automatically knows, but none of my friends will tell me. I just don’t know. I’m kind of a nerd, which most women aren’t into, but my friends and my brothers like the same things I do, and don’t seem to abnormal love-lives. I know I may come across as too straight-laced, but I’ve been consciously trying to work on it, and I don’t notice much of a difference.

I’ve never even been aware of a girl liking me. Not ‘there was a crush someone told me about from someone I didn’t like, and I didn’t reciprocate.’ I mean no one. I can’t even think of a time I noticed a woman being mildly flirtatious with me, other than women I knew weren’t single who were just naturally bubbly or joking. (I know you’d think, well, women won’t flirt because my self-consciousness must be subconsciously coming across, but I’ve been trying to act, um, “not-self-conscious,” and I’m doing the best I can!)

So my two big fears are (1) nothing has ever happened so far, so why should the next girl I like be any different? And worse, (2) even if by some miracle I get a second or third date with a girl I like, if something actually gets going down the road, there is no way she won’t eventually realize I have no experience and have little to no idea what I’m doing. And how is a woman going to react to that? If I was a woman, I’d have to assume there was something wrong. Is this guy actually gay? Does he have some weird background problem I haven’t found out yet? Is there something obviously wrong, and I’m just stupidly not noticing it? I can’t even imagine some things she might think. Even a fair-minded woman would have to. I mean, there is no way I’m going to be able to kiss a girl and have her not realize I’ve never done it before …. to say nothing else. How can I expect a woman to be patient with someone with the emotional experience of someone 10+ years younger?

I guess the question is, how bad is it? Should I ever tell a woman this? When? How? How do you hide it? Are you supposed to hide it? Hopefully I’ve wasted enough “ink” (or kilobytes) that you get what I mean ….
Last edited by FaintestInkling; July 8th, 2009 at 05:45 pm.
- July 8th, 2009, 05:42 pm
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FaintestInkling FaintestInkling is offline
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(I actually meant to post this in "Ask a Dating Expert" not "Dating" ... oh well.)

And, oh man, that does look long. I know someone will ask about something or other if I left it out though ....
- July 8th, 2009, 05:44 pm
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D_Lion D_Lion is offline
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D_Lion - Ladies want to wring my neck - you have been warned!

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I was nearly 25 before I had my first relationship. I think your inexperience needs no defense or apology – and avoid presenting yourself negatively in your communications. In my expectation, the right woman for you will not care about it, or even find it a positive. 27 is not young to form the relationship which becomes your family.

I do not consider it “disrespectful” to approach a woman; really, if you are sincerely interested in having a friendly conversation with someone to find out her name and something about her, that is a perfectly reasonable thing to do. And the more you do it, the more comfortable you’ll feel, and the more effective you’ll be.

I would guess you seem bland in a profile (I know mine did when I started), and I do think that makes the process go slower. Perhaps you can get in it some humor, and work on getting the right photos?

Welcome and good luck!
- July 8th, 2009, 06:02 pm
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meanminicooper meanminicooper is offline
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Hey, welcome man. No need to dance around it. You're one of the shy guys out there who doesn't believe in being a barfly, spitting game, the 3-day no-call rule, the call-instantly rule, hard-to-get, put on a badboy face and she'll like it. They are all games. its why I havent been on a date in 3 years and I could not be happier with my life. Im also at the age where most of my friends are married, engaged or raising kids.

So my best advice is when you interact with your friends, do so normally. Dont break routine or make special trips of situations. I know that on the few occasions in the last 5 years or so where i got decked out for a guy's night at a hunting spot, I ended up feeling so out of place that i left early. You want someone to appreciate you for who you are, not to transform some bar-hopping, MTV, bling bling model type to be into you because there will be no compatability.
- July 8th, 2009, 06:14 pm
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IcecreamMoon IcecreamMoon is offline
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IcecreamMoon Nothing to see here at all...

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Can I just invite all of you guys for an extended vacation on the Moon?

OP,
I gladly confirm every word of the advice here so far.
Welcome! And please feel free to join me on the Moon any time. Just bring some Ice Cream with you for some added pleasure
- July 8th, 2009, 06:23 pm
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LivingSunset LivingSunset is offline
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I think you need to relax and quit over thinking every tiny detail. You'll be surprised at how naturally everything will come to you once you meet the right woman. Stop worrying so much, you'll find the right person for you one of these days. You just have to trust that when the time and person is right, good things will happen.
- July 8th, 2009, 06:28 pm
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Wootz Wootz is offline
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Wootz Gone to the family reunion all weekend! Packing the medkit and riot gear...

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Man, ink, you sound like me when I was younger. So maybe I can give you what worked for me.

I won’t tell you to stop worrying. That’s kinda useless for me to say. I will say this: learn to flirt. Once you get going about something you are passionate about (remember that no.1 question in your profile?), you’ll notice (later) that you got calmer. Learn *how* to just be yourself. The real, *not* hyper-sensitive to what she says, *not* nervous as along tailed cat in a room full of rocking chairs, *not* over eager kind of you. Start having some boring conversations with girls, first. Get past the tongue tying. If you’re at the point where you can order a cheese burger, comment on the weather, and ask if she knows where the bathroom is without making an arse out of yourself, you’re already miles ahead of where I was when I started.

Back to learning to flirt. It does take practice if you are so very green to it, as I take it you are. Do you have any female friends now? Find the funniest, most social, most easy going one. And do pretty much what she does. Except make it a compliment. Confused? Lemme ‘splain. No, is too much. Lemme sum up.

Women share something with guys when it comes to compliments. Rule no.1: don’t go overboard. no.2: Be honest. no.3: be specific, but remember rule no.1. Practice makes perfect- or at least less awkward. When you see something that she does that makes you go "cool!" let her know right then. Insta-compliment.

One last thing. Take everything I said with a grain… heck, take it with ten solid ounces of salt. There’s probably a reason I’m still single ya know. *grin*
- July 8th, 2009, 06:50 pm
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pourquois-moi pourquois-moi is offline
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I suggest that you stay true to yourself at all times because thats the person you want your special someone to be attracted to. Continue to go out, all you need is one single friend to hang out with. I realize this may be difficult for you but you must show some interest when you see someone that you find attractive, whether its with a certain gaze, a simple hello or short phrase. Try to attend after-work events, join single groups and keep practicing how to make it flow; Just think casual conversation, no more, no less, if she's interested you'll know. Good luck and be patient!
- July 8th, 2009, 07:16 pm
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neardc neardc is offline
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You sound like a classic "late bloomer." That's really not a bad thing, though.

Believe it or not, you are not the first young man about your age to bring up similar issues here. I'm going to suggest that you look through one of the earlier threads (here: (28 yr old male in big social trouble) ) since you may find some of the discussion there helpful. You may also find a couple of the threads referenced in this thread helpful (here: ("I'm Still A Virgin: Does That Matter?"))

I'm struck by a couple of things. One is what a lot of people here have picked up on, and that is the issue of needing to acquire some social skills so you simply feel more comfortable with women and pursuing possible romantic relationships. Some of those skills can be learned simply by getting out there and practicing, even if it's just with the older woman behind you in the checkout line, or a stranger who happens to be riding the same elevator as you. You can start in situations that feel less threatening (i.e., where the focus isn't on meeting/dating someone), and then branch out as you start to feel more confident.

The other thing, though, has to do with the negative little messages that you are constantly giving yourself ("It's too late," "Why should I think the next woman could possibly like me," "I'm too inexperienced for a woman to want to be with me," etc.). You are doing a good job of convincing yourself that you will fail, despite your desire to move forward. One thing you might consider is seeing a trained cogntive-behavioral therapist to help you with this. This can help you learn to interrupt negative/harmful/destructive thought patterns and replace them with more realistic, positive ones. It can be quite difficult to do this on your own, especially once they take hold over a long period of time.

What is really great is that you have identified this as a problem for yourself and you want to do something about it! That means taking some chances and doing some hard work, but the payoff will make that all worthwhile.

Best of luck to you...
- July 8th, 2009, 07:29 pm
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Gr8Guyn2008 Gr8Guyn2008 is online now
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Gr8Guyn2008 I wanna know what love is, I want you to show me

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Twice your age and still looking for the first relationship
- July 8th, 2009, 07:48 pm
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