Almost 40-Year-Old Virgin

Monday, November 21, 2005

My first date ever

After my summer when I fell in unrequited love with Jenny, I returned to graudate school feeling miserable and still maybe somewhat suicidal. I tried to take up smoking, because I figured if I couldn't kill myself quickly, at least I could do it slowly. Fortunately for my health, I was never able to get the hang of it. When classmates saw me smoking, maybe it did just a little to shed my virginal nice guy image. Or maybe everyone saw right through that.

I decided that, if I couldn't have Jenny, the next best thing would be to find some other girl to love. Of course I had always been deathly afraid to approach a girl, but my relationship with Jenny revealed that at least a girl might be interested in talking to me. And it filled me with a great fear. I was afraid that I would never recapture the feeling of love, and although I have accepted that now, back then it was dreadful.

For a while this fear was greater than my regular fear of girls. I went out to a bar with some classmates, and I spotted a beautiful girl in the bar (yes, I know now that it was a mistake to only go after the pretty ones), and I caught her eye, smiled at her, she smiled back, and I engaged her in a conversation. She was a receptionist for a dentist. How lovely! How awesome it would be to have a beautiful non-college educated girlfriend. But alas, she made up some excuse about going to the bathroom, and I said something like "well you have to give me your phone number then," and she smiled and said no thanks. I didn't get a phone number, but at least I felt good about myself for going into battle.

I found out that there was going to be a social gathering at a campus religious organization. I don't think I ever really believed in the religion, but this was supposed to be a good way to meet girls. Once again, the fear of being alone the rest of my life proplled me to action. I felt like I was in a zone that evening, talking to all the girls at the social gathering, and collecting not one, but two phone numbers. Wow, I had never done that before.

But which girl should I call? My big mistake, of course, was not calling both of them. Dating is a game of percentages. But I was new to it. I had never been on a real date before. I called the girl who was the prettier of the two, a really cute undergraduate student with blonde hair and blue eyes, about 5'6" and 135 pounds. Her name was Madison. How cute.

It's hard to describe how overjoyed I was when I called Madison, and she actually agreed to go to dinner with me. After the phone conversation, I fretted over where to take her. I discovered a restaurant at a local resort hotel with singing waiters.

I suppose I overdid it. The waiters sang in a fun way not a romantic way, but nevertheless this may have been too much for a first date.

The date took a horrible downward spiral when the check came, and she didn't want me to pay for her dinner. Somehow, I knew this was a rejection. I argued over her with it until we agreed that she would pay the tip.

Thinking back on that date, it was so touching that she actually felt bad about getting a free dinner. These hardened bitches in their mid thirties in New York City, such as Sarah, have no problem with enjoying expensive meals from men that they have no interest in.

Madison hung out with me on the grounds of the hotel after the dinner, and while we were sitting by the pool, with palm trees around us, we were both looking up at the sky and we saw a shooting star. This was the first and last time in my life that I ever saw a shooting star. It really helped to mark the evening as special.

Looking back on all the dates I've been on since then, my first date ever was also my best date ever. I think that some of the love I felt for Jenny I was able to transfer to Madison, so this date was the closest I ever came to going out for a romantic evening with someone I loved.

When I dropped her off at her apartment, I tried to kiss her on her lips, but all she gave me was her cheek.

Madison didn't want to see me again after that.

My fear of being alone subsided shortly after that and once again became less than my fear of girls. Once again I was too afraid to ask girls out on dates. I was never again able to recover that strange feeling of fear and hopelessness that gave me courage.

17 Comments:

  • I was touched by your story until I got to this line, "These hardened bitches in their mid thirties..." Wow. There is a lot of anger in that statement. You got where you are because of fear and shyness, but you may be stuck there because of anger and resentment. I hope you can figure this out.

    By Blogger Jamy, at 11/22/2005 10:39 AM  

  • I think maybe Madison didn't want you to pay for her dinner because there is great confusion these days (at least in my world) whether I should pay for my dinner. I work so why shouldn't I pay for my dinner or drinks afterwards. I always offer. I think that's how I scare men away. I am too damn independent.

    You are not the only man or woman that is afraid of rejection. I am afraid of rejection but for some reason I keep on putting my neck out there. Nothing risked, nothing gained. The next time you find yourself wanting to talk to a woman but the fear keeps you from doing it, keep in mind that could be the love of your life.

    By Blogger Sky, at 11/22/2005 1:37 PM  

  • There is not a single woman in her thirties in New York City who has the least doubt about who should pay. The man.

    There was a Maureen Dowd column in the NY Times recently about this. I can't stand Maureen Dowd, but she was right when she said that women expect the man to pay for dinner.

    Because Madison was young and naive, she felt guilty about accepting a free dinner from someone she wasn't interested in. In retrospect, that's so touching. She was such a nice girl.

    By Blogger Almost 40-year-old virgin, at 11/22/2005 7:36 PM  

  • There is not a single woman in her thirties in New York City who has the least doubt about who should pay. The man.

    I'm sorry, I just don't buy it. I don't live in NYC, but if I moved there I would not expect a man to pay for me. I don't think that Madison is the only nice person in the world. She's certainly not the only nice woman you've ever met.

    I've said it over and over, but I always sincerely offer to pay my share (at the least). If I've been treated, I will pay the next time we go out.

    It's annoying that you slip into these stereotypes so easily. Maureen Dowd does not speak for all women.

    By Blogger Jamy, at 11/23/2005 2:47 PM  

  • When Brady and I first started dating, I asked him to please stop paying every time. I felt like he was going to go broke feeding me. He told me he was raised that the man pays, and that was just how it would be. So, as a compromise, I quit fighting him over the bill, but I do the cooking when we stay in.

    Not all women are hardened bitches, and although statistically there might be a LOT in New York, I'm certain they are not all that way.

    By Blogger Princess Helen, at 11/23/2005 5:44 PM  

  • I'm just a little confused by this "hardened bitch" sentiment. It kind of sounds like you think women who accept a meal owe something to the guy who bought it for them. I always offer to pay for at least my portion of dinner and drinks, and if a guy insists on paying, I don't feel like I owe him anything.

    I'm not going to lie, I like free meals every now and again. I know very few people who wouldn't like to get a nice free dinner every now and again.

    But most women I know, myself included, aren't going to put up with a guy we don't like just to get dinner. Because usually if I don't like a guy, I don't want to hang out with him, so I wouldn't be at dinner with him in the first place. And in the awkward instance that I determine over dinner that I dislike someone, if he insists on paying for dinner, I feel a little bad, but I'm not going to lose sleep over it. And I'm certainly not going to feel like a "hardened bitch" for it. You're an adult, no one can force you to pay for a woman's dinner.

    From my reading of your blog, it doesn't sound like you think very highly of women at all.

    By Blogger charming, but single, at 11/24/2005 3:08 PM  

  • Came by accident but I put you on my side bar so I can read you every chance I can get. Hope you had a nice holiday. Peace out, Prairie Girl

    By Blogger Moonchild, at 11/24/2005 11:52 PM  

  • PS: I am a 38 year old chick.... as to who pays? I usually end up paying.... It's no biggie.... That way I don't have to give in to the kiss or anything else ..... and guys like it.

    By Blogger Moonchild, at 11/24/2005 11:54 PM  

  • Just found out about this blog, and am really enjoying it! I appreciate the fact that you can be so honest and open about all this. Trust me I can relate!

    By Blogger Larissa, at 11/30/2005 10:13 AM  

  • As a woman in her late 20s, I always offer to pay my portion and 8 times of of 10, am rebuffed. I don't feel the least bit guilty in receiving free drinks or a meal, etc. If a guy is going to hold that against me, he's not someone I want to see again. When I get to the second or third date, I usually insist on picking up the tab for a movie or whatever, as it's only fair.

    as for sitting through a free meal even if you don't like the guy...no. You accept a date b/c you might be interested and the date is to see if there is genuine interest. I think it's better to tell someone you aren't interested than just ignore them from here on out. It can be depressing yes, but wouldn't you rather know?

    By Anonymous Anonymous, at 11/30/2005 3:51 PM  

  • Just out of curiosity, do you ever Google any of your former love interests (Jenny, Madison) to find out what became of them? And how many years ago was this?

    By Anonymous Jake Lee, at 12/26/2005 12:16 AM  

  • "do you ever Google any of your former love interests (Jenny, Madison) to find out what became of them?"

    Jenny has a very distinctive last name. She doesn't show up in Google at all. Very weird. I think she may have had some mental problems and wound up being a failure in life.

    Madison: I don't know her last name. I don't think one date qualifies as a love interest. Once I bumped into her in a bank, but she didn't remember my name.

    By Blogger Almost 40-year-old virgin, at 12/26/2005 9:31 PM  

  • I live in NYC. It's a really big place. Lots and lots of women in it. I promise you that they all aren't out for a free meal.

    More to the point, though, what the above posters said: your paying for someone else's meal or anything), regardless of your gender, doesn't mean the someone else owes you *anything.* And by the way, the reason that woman didn't want you to pay was probably because she suspected that you, like a lot of men who still can't or won't get this, would hold it against her if she accepted. Never even mind the implied expectation of "putting out.* No meal is worth being on the receiving end of the resentment you're putting out here. That's like being asked to swallow poison for dessert.

    Seriously, if you really believe in the transaction approach--"I pay"="you put out,"--then do yourself and the women a favor and be straightforward about it. Hire an escort. That's what they're there for. Yeah, they'll charge more than the price of a dinner. But if that's your main complaint, face it, your problem isn't the principle of the thing, it's that you're cheap. You earn a six-figure salary, you said. Swallow your pride and just do it.

    By Anonymous Anonymous, at 2/12/2006 12:26 PM  

  • I never ;et guys pay for my dinner on the first date even if I really like them. I never have either.

    By Blogger Lauren, at 7/13/2006 1:41 PM  

  • Always let the woman pay for dinner if she wants to pay. Gosh. That's even a good sign if she wants to pay.

    By Blogger Spanish Prisoner, at 8/31/2006 12:11 PM  

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    I like your story.
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    By Anonymous Anonymous, at 2/09/2007 9:47 AM  

  • There are many things in your life that you refuse to accept. Unfortunately love sticks around because of the things we choose to accept and tolerate.

    I don't think it's fair to say you are judgmental. I think it is funny that a lot of the people who call you that on here come across the same way.

    My question is more about tolerance. Fear cuts the process short. I can't tolerate someone or something that makes me feel weird inside. If I can't even begin to tolerate what someone else does/is because I can't get past how they make me feel, then I need to start with the fear... ask questions about it. Why am I afraid? What is the risk? What is the cost of opportunity?

    By Anonymous Anonymous, at 5/02/2007 2:30 PM  

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