Skip to content

Simply Solo Spotlight: Tips for Dating Your Ex’s Best Friend

September 25, 2012

Today’s Simply Solo Spotlight is brought to us by Paul, a writer from, a great resource for all things related to babysitting. Paul and his wife Julie both spend quite a bit of time coming up with ideas, blogging and researching childcare. Since kids really aren’t the focus area of Simply Solo, Paul has offered his advice on how to go about dating your ex’s best friend.

Quick shameless plug: Do you have a story to tell? Advice to offer? Did you just have literally the worst date of your life and you must write about it? I’d love to have you as the next Simply Solo Spotlight! Find out how you can be the next writer for Simply Solo here!

Tips for Dating Your Ex’s Best Friend

It may not be the kosher thing to do post break up, but sometimes you can’t help but falling for someone you least expected. Your ex-boyfriend’s best friend. These things happen; it’s more common than most think. It’s a sticky situation and if not handled properly, it could leave you with two exes, instead of one. Here are some tips to help you date the forbidden best friend:

Notify: OK, so you don’t think your ex even deserves the right to know that you are now dating his best friend and frankly, he probably doesn’t deserve to know. However, our mothers taught us better and we should just take the mature, high road that we all hate. To save yourself from any further and unnecessary ex-boyfriend drama, have your boyfriend (ex’s best friend) sit his best friend down to let him know. Trust me, your ex would rather hear it from his bro than from his ex-lady friend.

Don’t gloat: The first thought for your ex and anyone who knows you and your ex is that you are dating his best friend to get back at him. If that’s the case, shame on you. But if you have fallen for him legitimately, that’s great! Just don’t gloat. Remember to be mature about it.

Okay, so you probably will never have THIS kind of relationship. But don’t break up bros. It’ll come back to haunt you. (Photo courtesy of Ryan Jones)

Don’t make him choose: Never make a man choose between his bro and you. Bro code is stronger than you think, plus messing up a friendship can really come back to haunt you. Your boyfriend probably is having a hard time as it is dealing with the feeling that he took his best friend’s girl. Be supportive and allow them to be friends.

Stay out of it: Whether they will remain friends depends on the break up and the level of friendship that your boyfriend and your ex have. In some cases, it won’t faze them, and other cases, they’ll say “peace out” faster than you can say “jealous much?” Let the boys handle it and stay out of their friendship.

Stay private: Your ex and your ex’s friends don’t need to know all the little deets about your new relationship with the best friend. The less they know, the less they will think differently about you, ask questions or tsk tsk in your general direction.

Don’t compare: It may be hard to not naturally allow your mind wander down the comparative road. Make a conscious effort to keep your ex and your boyfriend separate. Just because they are best friends doesn’t mean they are the same or that one did something better than the other. You are starting fresh – keep it that way.

Don’t be ashamed of who you have fallen for and remember that you are grown adults who can make decisions that benefit yourselves. Your happiness matters as much as your ex’s, so do what is best for you and your new boyfriend. There will be challenges, but the long road will be worth it. Good luck and happy dating!

Copyright 2012. Simply Solo blog by Catherine Gryp. All Rights Reserved.

9 Comments leave one →
  1. Jeff W. permalink
    September 25, 2012 6:47 pm

    Tip #1 … Don’t do it. The end.

  2. September 25, 2012 6:56 pm

    “Never make a man choose between his bro and you. Bro code is stronger than you think” Um.. if bro code is stronger than you think, then I doubt a scenario like this would happen, even under the best of circumstances… if it does, I doubt “bro code” is something the girl would have to worry about at all…

  3. Lorraine permalink
    September 26, 2012 5:55 pm

    This post is disturbing. I didn’t know there were “tips” on how to lack character.

  4. Hadley permalink
    September 27, 2012 10:10 am

    I find this article very interesting and something I can relate too. I am dating my ex’s best friend. Gasp, I know- I have no character. I dated my ex for 6 years, we bought a home and picked out rings, we had a great relationship but his heart was elsewhere and he left me to be with a different girl. I was blindsided and devastated. I have kept my friendships with his, our and my friends, as well as he. I never thought of his best friend, in fact, I almost found him annoying and disgusting. The best friend lived 5 hours away and other than the occasional comment or post on FB we were nice to each other. Then I randomly ran into him at a friend’s event. We chatted after not seeing each other for 2 years and something happened. There was a spark. By this time my ex of 6 years was engaged. The best friend and I tried our best to move on and not talk to each other because we both felt it was odd. Then one day we said what the hell. The best friend called my ex and told him the news, my exes response was in shock and then after a few minutes said ‘well you know what? I can see that, you guys will be happy’. That was 2 years ago, the ex is married and happy and I am happy with the best friend. The boys live in different cities but are still friends and know how to keep some things separate. Have things changed between them? Of course. Do I feel badly about it, yes and no. No because who know after all these years that gross and annoying best friend would turn out to be MY best friend and the person that makes me laugh and smile on a daily basis.

  5. September 28, 2012 12:34 am

    Thank you everyone for your comments. As it may seem like a huge no-no in the guy world, however it does happen based on the fact you can’t help who you fall in love with. It is possible and has happened. I believe and know from experience that as long as everyone involved is aware of what is going on and handles it sensitively as adults, all is fair in love. Again thanks for the comments.

  6. April 9, 2013 10:01 am

    My best friend started dating my ex after we broke up. I literally wanted to murder him and we didn’t talk for six months. But go a head and make your ex feel like that. That’s probably what it’s all about since your relationship is probably nothing more than a fling.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: