Biggest Dating Regrets

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I went through a phase where I regretted just about every move I made in dating, from cold hitting on a girl, to sex, to committing (in fact, I still regret half the moves I make). Is Truth in Breakups Overrated?


One Night Stands

It seems like such a good idea at the time, but in the aftermath you're mostly thinking: "I shouldn't have done that" most of the time.


Sex To Early

Even when you're dating someone, if you have sex too soon (especially as a woman) you have to go through that period when you're not sure if he'll stick around because he was only after sex.

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Taking Back The Ex

A friend of mine at work has taken her ex back five times. We all gave her a hard time when she announced she took him back again. I guess she copes with regret well. In some cases, we do feel bad when we take back the ex just once and they turn around and do the same mean thing to us again.


The One That Got Away

Perhaps someone likes you at one point. You take it for granted and think they will always be around. I did this with a girl who had a crush on me all through middle school, and then when I was ready in college, it was too late.

Not Making An Effort

Often, I see a super cute girl in the cafe or on the subway and I make up all sorts of scenarios about how I'll make my approach. In the but all I'm left with is the fantasy of the girl on the subway.

Saying Stupid Things

How many stupid things have I said to women? It's far too many to count. Many times, the failure is even more acute because I have a habit of doing well for a while. So, I set up a nice structure to destroy. Usually, I'm cruising along and I say a record-scratching horrible thing that I think is so amazing. But once the girl walks away, slaps me, or cries, I realize I made a mistake and I'm left to lament my big mouth.

Dumping Someone

Sometimes it has to be done, but you regret it if you have feelings for them later.

Believing/Trusting Someone

It's so tough to gain trust, but so easy to break it. Many times in relationships, believing a person is a leap of faith because so many people are dishonest. When you find out you've been lied to, it's that much tougher to trust the next person.

What have you regretted in dating and what do you think of my list?

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