Your Call: How Do I Re-Enter the Dating Pool?

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We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call on the letter below by leaving your advice in the comments section. 

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Dear Em & Lo,

Five-ish months ago, I broke up with my first boyfriend. Obviously, there were problems, but it was a really significant relationship. And, there were some really great things about it: the sex; the emotional and intellectual chemistry; feeling sexy, attractive, and flirty; etc.

About two months post-break up, I figured it was time to re-enter the dating pool. I didn’t want to lose the “I’m sexy, attractive, and flirty” feeling I had in the relationship. But, the more I dated, the more crazy, desperate, and insecure I became. Also, the more I dated, the more I missed the ex. I figured it was in my best interest to stop dating, truly get over the ex, and be alone until I was okay being alone.

I sort of miss the ex from time to time, but that’s pretty much over. However, I really hate this being alone stuff. So, my question(s) for you is this: How do you re-enter the dating pool? How do you get out of the I’m-lonely-and-just-want-someone-to-cuddle-with phase and back into the how-many-men-can-I-seduce-tonight mode?

— Water Wings

What should W.W. do? Leave advice for her in the comments section below.



  1. Water Wings,

    Figure why you want a relationship. Do you want to just have fun or are you looking for something more serious?

    If you just want to have fun, figure out what you enjoy most and how you can have fun doing it. Generally, people who bump into the love of their life meet that person while doing things they both enjoy.

    If you like to hike, join a hiking club. You’ll enjoy yourself and you might bump into Mr. Right there. Now, you are having fun, found someone you like and you two have something you love to do together, just like that!

    If you are looking for something more serious, build your confidence. Seeing as how this was your first relationship, I am daring to say you are young. When you are young (early 20’s), it’s hard to find men who want serious relationships. Definitely not impossible, but hard. When you want something serious and you don’t get it, it can be disappointing.

    If you go into the dating pool looking for something serious, don’t accept just any guy. Think about what you want out of your significant other. Be realistic though, or you’ll never find him. Having a standard for what you’re looking for will help you not waste time.

    Re-enter the dating pool confident, excited, hopeful and knowing that you are the best thing that will happen to some lucky guy.

    Also, remember no guy thinks, “I want to hangout with that lonely girl!” Make sure you look like you’re enjoying life!

    Best of luck,

    Eight at Eight Dinner Club

  2. First relationships take a really long time to get over, and leave you with more baggage than subsequent relationships will.

    Normally I think that casual sex is a pretty great way to at least treat the symptoms. But don’t force that if it’ll make you feel worse.

    I say just get out there socially – hobbies, nights out with friends, etc. That’ll keep your mind busy, while leaving open the possibility of a new relationship (romantic or just sexual) developing organically. Something about the, “I’m dating again, damn it!” mentality is counter-productive a lot of the time.

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