Why am I such a failure at dating? (long)

[delstar]

Hi, sorry if this doesn't make a lot of sense but it all should tie together at the end. If you really get tired of my post, scroll down a bit, the actual scenario is there.

 

Long story short: I can't get myself to ask a lady I know would go out with me, to actually go out with me.

 

Long story long:

I'm not normally a very shy person.

 

I've sang in front of 2000 or so people as part of my HS graduation and work in finance dealing with clients placing large equity stock orders. I'm an excellent conversationalist, have a fantastic memory and can carry conversations on a large multitude of topics ranging from political instability created by the Asian financial crisis (I was a Poli Sci major) to my theories as to why oil prices are through the roof and why we're all screwed to betting on pro football in Vegas and how quantitative the lines are.

 

I've done all three just this past Saturday, at length.

 

So, that being said, I'm a fairly confident person. After being insecure through most of my life with a nasty combo of ADHD and depression-related issues (I've been diagnosed with pretty much everything except schizophrenia), barely getting through HS, I went to one of the best colleges this country has to offer via junior college. College brought out the best and worst of me but I'll skip most of that.

 

After graduating college in California, I moved out to Delaware and got my job in the world of finance, but most importantly, Delaware is closer to most of my family and I was wanting a change of scenery. A lot of what little I learned about dating came from my friends, most of which are rich Asian ballers from growing up in my San Diego suburb. We'll meet up in Vegas and the 10 of us will drop $4k a night on alcohol in the VIP rooms at the clubs, hours after winning $3k on a LSU football game.

 

In my free time, I travel... around the world. This year alone, I've already been to Hong Kong/China; California twice and Texas for various reasons. My passport already has extra pages added and it's still good for three or so years. I also don't travel for work, it's all on me. I already have tix booked to go to California again, Louisiana and Japan. That's all before October.

 

This is going to start to tie together..... stick with me.

 

I'm saying that for a reason - no matter what I do, how baller I look/act/really am in reality, I can't get ANYWHERE with ladies. Nowhere. Nothing at all. I haven't felt this good about myself in years... maybe ever. I'm going to surely tell that I'm not the most physically attractive person out there.. I'm at about 6'3" 255lbs which is a big improvement over the 300lbs I was previously.

 

Now, don't get me wrong, I'm not trying to be someone I'm not. I'm not some billionaire mafioso or anything, I'm a chubby white nerd with a goofy set of accents, wears visors, has a huge interest in foreign cultures and listens to electronic music. I don't hid this at all. I don't pretend to be some gangsta or douchebag socialite-type person. I typically spend most of my weekends at home watching baseball and reading books on futures trading.

 

So what's my problem here? I'm obviously confident enough to do whatever I want and not care about what others think. I'm smart enough to appeal most anyone with working ears. I'm not the world's most physically attractive person but whatever, I make it up with a polite and forgiving attitude.

 

I can count the number of dates I've had on two hands with my life. I'm 28 years old. Those 8 or so dates were with two people, last time was ~4 years ago.

 

There's this lady I know... she currently is seeing someone but a close friend of mine and hers told me that she was tired of this dude's crap as he's some sorta pretty-boy douchebag who's a few years younger than the lady I know. This same close friend told me what she looks for when going on dates... everything from offering her some of my food if I like what I ordered to touching her lightly. He knows her well (he also dates her close friend but I digress) and basically gave me ALL the answers to the test. I'm showing up for a midterm with the answers written for me by a professor's assistant who will be helping the professor grade the test.

 

Yet, I STILL cannot get the nerve to ask her out. I cannot figure out what the problem is! I do think it's a combo of three or four things:

 

-Lingering insecurities: As stated, I've had all sorts of problems in HS in many ways. I still have a serious case of ADHD and take medication for that. It's often the butt of jokes with me, but it doesn't change the underlying problem. Plus, i'm still flabby, not Fabio. A lot of it is that I have a poor physical image of myself but whether thats actually true in ladies eyes or not is another story. Also, I'm not a "trendy" kinda guy. I do my own thing and hate looking like a douchebag clone at the club with the untucked button down shirt and dark black-ish jeans.

 

-Fear of not getting what I want: I'm used to getting what I want. I'm not a spoiled brat in the sense that my first car was a BMW and I wrecked it, cried about it and forced daddy to replace it with a Mercedes (FWIW, my first car was a Civic that I drove for 270k miles and now a Toyota Corolla). However, I pick my battles VERY wisely. I will NOT get into a situation where I will be told "no." I don't mean in the sense like playing a video game with friends or bowling... but when it comes to my goals, I make them happen. I got into exact college I wanted to go to, I got the exact job I wanted when I graduated in the exact field I want to be in. Basically, I do not expect to be told "no."

 

-Lack of experience: I'm just figuring this crap out when most people were when they were 16. That's pretty sad. I typically embrace challenges and hit them head on. Why I can't even being to face this is beyond me. I'll do some very gutsy things (see the LSU bets in Vegas) but can't do something so simple where the worst that can happen is that I just move on.

 

I'm truly stuck. The lady I'd be asking out in this situation, want someone who is mature, intelligent, loves to travel and is kind and polite. That's a 100% fit. Why is this so hard for me to even suck it up and go for it is beyond me. When I was young, I got no play, trust me. I suppose I may have some deep down repressive fears that I'm unwilling to face.

 

We're supposed to be doing lunch later this week (she works near me) but the thought of asking her out and not to a lunch break salad bar with my cell phone ringing in the middle of the lunch 3x frightens the living daylights outta me.

 

Wow, sorry this is so long. I'm seriously considering professional help for this. I should print this out and give it to a therapist I think this would probably answer all the questions he/she would have when doing the standard introduction and questioning.

 

Any insight is appreciated. Thanks!

 

ps, I know I sound like I'm bragging but in a way, I am but it's also important to see not just who I am now and where I'm at, but where I came from and how I think it is influencing my current issues.

 

This has also been fairly therapeutic.

[eurocar]

First off, welcome to ENA.

 

Now I'll dive right in. You're a failure because for the longest time, your identity revolved around failure (or the perception of it, at least). Now that you appear to be thinking more highly of yourself, you can really begin to take these additional challenges head-on. But, we don't change in a black-and-white, on-and-off sense; our changes are fluid and because they are both initiated and directed inwards, it is natural to have some leftover "residue," fallout, whatever you want to call it, from previous states of mind. For you to still have some insecurities would not only be normal and expected but actually quite critical to your sanity. If you went from being a clinically diagnosed, chronically unhappy hermit to someone with no insecurities or self-perceived faults whatsoever, I'd say there was something wrong with you. So it sounds like you have a good head on your shoulders, a great career track, and are generally playing your cards right. What do you have to lose? Hold your head high and don't evaluate the "worst-case" scenario. It's pure bullcrap, because it hasn't happened yet; it is one of the biggest components of insane thinking (worrying about that which has not yet happened) and you have neither no right nor no reason to ruminate about what "might" happen. Because, chances are (and when I say chances, it is only "chance" for the sake of convenience--it's quite literally a 99% chance) it won't happen the way you picture it happening. Trust me.

[iwishiknew]

I feel like I am a failure at the dating scene, because I have not had a date yet.

[delstar]

tomorrow's game time... at the plate for the average guys... delstar.