• Give a Gift
  • Customer Service
  • Promotions
  • Videos
  • Blogs
  • Win
  • Games

Biggest Dating Regrets

Posted in:

Biggest Dating Regrets


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.

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?

Connect with Marie Claire:
daily giveaway
Go to the Beach

Go to the Beach

enter now
You Know You Want More
Special Offer
Link Your Marie Claire Account to Facebook

Marie Claire already has an account with this email address. Link your account to use Facebook to sign in to Marie Claire. To insure we protect your account, please fill in your password below.

Forgot Password?

Thanks for Joining

Your information has been saved and an account has been created for you giving you full access to everything marieclaire.com and Hearst Digital Media Network have to offer. To change your username and/or password or complete your profile, click here.

Your accounts are now linked

You now have full access to everything Marie Claire and Hearst Digital Media Network have to offer. To change your settings or profile, click here.