Here's what it's like to date someone much more attractive than you

This answer probably depends a lot on how much better looking the person is, and how good looking they are. The larger the gap and the better looking the person, the more of an impact their looks could have on the relationship.

I went on a date with the best looking guy I have ever seen in my life. And it went horribly. I acted like a complete idiot. I was totally insecure around him and completely self-sabotaged.

I first met this guy in the early 2000s when I was in my early twenties. I worked on a swanky trading floor with a a lot of young, good looking people. And the most gorgeous view of downtown San Francisco. Money and bravado sloshed around. There were also a lot more men than women, so the odds were in my favor. I was in great shape, and confident: I wasn’t desperate for attractive dates, or attention from good-looking guys.

Yet, there was one guy who was clearly the best looking guy at the firm. Let’s call him B. He was the best looking guy I have ever seen. I’m not exaggerating. Unbelievably gorgeous.

I’ve seen Tony Gonzalez, the American football player, with his shirt off before — his body is other worldly — he had muscles bulging I didn’t even know existed. Next level. Like Tony Gonzales, B was in a different league from others — even other really good looking people.

Typically I’m attracted to people based more on their personalities, sense of humour, and how they make me feel. Never in my life had I gotten a serious crush on someone based solely on their physical looks alone.

I knew nothing about B apart from how he looked. Yet, I continually asked mutual friends to set us up. He was never interested. I took every opportunity possible to talk to him. I was not discreet, and tried to catch his eye whenever I saw him. I even winked at him once.

This was before social media (although we did have work BlackBerries), so all of my oogling was in the open. I rarely went to happy hours after work — because we started work so dang early. Yet, if he was going, I went.

Fast forward a few years: the dot-com bubble burst, the investment bank went out of business, and we were both out of a job. I went to a cafe in the middle of the week, and saw B. I felt a little embarrassed after I had been so obviously throwing myself at him for years, but I went ahead and got my coffee.

I took the seat right next to him. Old habits die hard.

B was reading the New Yorker, and I knew a bit about the author he was reading. I made a comment (couldn’t help it), and he looked over and introduced himself! I was pretty shocked he didn’t remember me at all, but figured it was for the best. We talked comfortably for about an hour. He shared his chocolate chip cookie with me. And he asked for my number.

I figured he would never call. Yet, he did. That very next morning! He was charming and funny. He asked me if I had plans for that night and asked if I wanted to go out with him. I did have plans. But immediately cancelled them to go out with B.

We went out to dinner, and it started to go downhill. As other people have mentioned, it can be a strange and uncomfortable experience when you go out with someone so much better looking than you. People treat you differently, and the dynamics can be weird.

First of all, it was Friday night and we were going to the most popular restaurant in town. We didn’t have reservations, and I didn’t think we would get in. Of course I didn’t care where we went. But B was confident it wouldn’t be a problem. He “never made reservations and always seemed to get a table". Sure enough, we walked right in, and got one of the best tables in the house.

All eyes were on him. People (men and women both) at the tables next to us couldn’t stop staring. The waiter came up, and said to him, “Wow, you are good looking” then looked at me with a “hmmm, ok” look. Another person came up and asked him if he was Pete Sampras or "someone else famous".

The waiter was so distracted he completely messed up our order. We also got a nicer bottle of wine than we ordered. I don’t know what we were charged, but I’d guess we didn’t pay full price.

Throughout the dinner it was hard for us to have a moment to connect as people kept interrupting our conversation. B seemed annoyed —but not surprised — by the attention.

A group of women came over uninvited and sat at our table! They complimented B on his shirt (it was a plain blue shirt that looked good only because it matched his gorgeous blue eyes), and proceeded to flirt with him until he had to ask them to leave. They giggled and gave him their number. All while I was sitting right there.

I started to get really uncomfortable and insecure. I was so desperate to keep his attention but didn’t know how to act. I was not myself and felt horrible afterwards. It was really awkward when he left.

I never saw him again. He called me a few times, but I was too insecure to even pick up most of the time. When I did pick up, I was an anxious mess. Once B called me while I was heading out to an interesting lecture. He was interested in coming to hear the speaker (a local author). If it were anyone else I would have asked them to come join me.

Yet, I was worried I didn’t look good enough that day to invite him. So, I blew him off and acted strangely. I was simultaneously desperate and insecure. Not an attractive mix. It was stupid, because he seemed more interested in literature and conversation, than in what clothes I was wearing. Yet, I couldn’t stop worrying about my appearance. Typically I am not like that at all.

Bottom line: I acted stupid, and it was horrible for my self esteem. I analysed every detail of this date for months, and bored all of my friends with the same story over and over. Ultimately, the experience was no fun.

Relationships are typically best when you can be yourself, and the relationship feels natural and balanced. When things are off balance, whether due to imbalance in looks or something else, it can create a strange dynamic. As others have mentioned, it isn’t rare to see successful men date younger women who are much more attractive than they are. Successful men often “balance” out their looks with money, success, power, etc. How else could Donald Trump end up with a super model?

Surely, there are also attractive people who are completely full of themselves. I’ve also dated a few of these types. They are a pain in the ass to date if they perceive themselves to be better looking. These types actively search out attention and are more likely to cheat, etc.

Yet, again, when talking about the absolutely best looking person I dated, it was me, not him that acted weird. B didn’t seem arrogant or full of himself. Instead, he was more guarded and slightly shy. It could have made me feel better about myself, and I’d guess many people’s self esteem rises when they date someone better looking. After all, the "matching hypothesis" says that, “people are more likely to form and succeed in a committed relationship with someone who is equally socially desirable. This is often researched in the form of physical attraction". So certainly many people probably feel an increase in self esteem when they date someone really attractive.

Ultimately, it probably depends a lot on why you are dating this person, and generally what you value in a relationship. It is possible to date someone really great looking, but not even date them based on their appearance. For instance, it could be that you fall for someone based on their personality, and they just so happened to be better looking, but it isn’t the sole motivation for the attraction. And certainly the more you get to know, and love someone, the better looking they get.

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