Obviously if you handle this wrong, you can ruin a friendship and a potential future with a great romantic prospect. Although there are concessions that can be made that is dependent on how long the two of you have been friends, the extent of your friend’s relationship with the girl/guy (i.e. dating, committed, living together, etc) and how long was the happy or unhappy couple together? I tend to think more men would be ok with their buddy dating an ex than the ladies dating each other’s ex. Rule number nine In my book, The Straight Man’s Pocket Guide to Picking Up A Hottie-Written by a Woman Who Loves Women, states that “hotties are everywhere”; meaning someone that you may be interested in is potentially everywhere. Look around you, pay attention or you may just be missing out on someone. So with that rule in mind, you may want to steer clear of the whole idea of dating your friend’s ex to avoid any problems. However, If you can’t let it go, then the following are general guidelines to consider if you really want to date your friend’s ex:

• Regardless of the extent of the relationship or the length of time your friend was with the ex, make sure your friend is completely over this person before you go for it. Talk to your friend and see where they are with the break up and how they would feel about you asking their ex out. Get the ok to go for it from your friend. Do not date in secrecy. If your friend says “no” to the whole idea, let it go and just move on-that’s the bottom line

• Do not open the floor for discussion with your friend until a minimum of six months has passed.

• If your friend gives you the go ahead to ask their ex out, make sure you do not discuss anything about their relationship with this new dating interest. It could get awkward if he/she wants to bring up things that your friend did during their time together. So clearly agree to not discuss their former relationship. There are so many other things to talk about. Focus on the two of you to find out what you have in common with each other, learn about their friends and family, and what their passions and dreams are.

• Although this tip can be included in the one above, it is so important, I am calling it out separately. If you and your friend’s ex manage to end up having sex together, do not ask them if you are better sexually or like sex with you better than your friend. Do not have any comparison sex talks; even if they bring it up, do not do it. Tell them you are uncomfortable with that type of conversation and move on from the topic.

• Even though your friend gave you the go ahead to date their ex, be ok with a conversation from your friend if they should ask you how your first date with the ex turned out. Don’t bring it up on your own, but if they ask and without over embellishment, tell them you had a good time (if that is the case) and leave it at that. Don’t go hog wild and share every detail about it and that you are over the top crazy about your friend’s ex already. Be calm, cool, and reasonably collected about it.

• If your friend’s ex flirted with you at any time during their relationship, do not agree to go out with this person. You should have told your friend that their girl/guy flirted with you back when it happened. Nothing you can do about the past but you can choose not to go out with someone who would exhibit this behavior. Seriously, why would you want to date someone who flirts with other people while they are with someone? Bad idea. If they did it once, they’ll most likely do it again.

I realize that sometimes we get into dating slumps and think that we’ll never meet anyone that interests us enough to go out on a first date. Getting to know someone new is hard and sometimes someone new could be sitting right under your nose; your friend’s ex. Just because their relationship didn’t work out, doesn’t mean it will not work out for the two of you. If your friend gives you the clear go ahead to date their ex, go into it with fresh eyes and an open mind. Get to know them through your eyes and through your experiences and have a good time learning new things about them.

Cheers,

Robbie Lee, author of The Straight Man’s Pocket Guide to Picking Up a Hottie-Written by a Woman Who Loves Women.

Sign up for my mailing list at Robbie411.com

Rate This Post:

Did you like this article? Submit it to your favorite social bookmarking sites:

About The Expert

On our About the Expert page, you can learn more about the author, including contact information and other posts they've written. About Robbie Lee.