How to... Date a Friend's Ex-Girlfriend

by Michael Pollick

Dating a friend's ex-girlfriend can be one of the trickiest scenarios a single man could possibly face. The arrangement is often fraught with peril, since one wrong move or misinterpretation can cost you both a good friend and possibly the love of your life. If you feel you must pursue the relationship despite the personal history between your girlfriend and your buddy, remember to tread lightly until your relationship is fully established. Your friend may or may not come to terms with the new arrangement, but ultimately that's his problem, not yours or your girlfriend's. If their relationship is truly over, she should be free to date whomever she pleases. As a friend, however, you do have an obligation not to rub salt in your buddy's wounds, so you may have to play down public displays of affection or discussions of the future around him out of mutual respect. If you do choose to pursue a romantic relationship with a friend's ex, here's some advice to keep it from becoming too awkward or damaging to your friendship.


Seriously consider not doing it. This may sound harsh, but lifelong friendships don't grow on trees and you may be risking too much over one relationship. Your friend may have been your friend long before he started dating his ex-girlfriend, and you could easily cause a major rift if you pursue a relationship with her. There are plenty of available women in the dating world, so you'd better have a very compelling explanation why it has to be her and no one else. It really doesn't matter if they broke up yesterday or ten years ago, it could still feel very awkward to see an ex-girlfriend in the arms of someone he knows very well. If you value your friendship, you may want to grit your teeth and break off your plans to pursue your friend's ex romantically. This doesn't mean your feelings towards her are invalid, but out of respect for your friendship you need to avoid causing unnecessary pain.

Make sure the relationship is truly over. You may have had a unrequited crush on your friend's girlfriend for years, but you shouldn't act on it the day after their last "big fight." One or the other or both might come to you for advice or counseling or sympathy following a break-up, but don't confuse this with an opportunity to pursue your own agenda. If you and your friend's ex do have a solid rapport with each other, waiting a few months shouldn't hurt your chances. The worst position you can be in is to make romantic overtures towards the ex shortly before your friend reconciles with her. Now she realizes how you truly feel about her, and this information could reach her boyfriend's ears. You are not going to come out looking so good. If you want to ask the ex out on a date, make sure the relationship is definitely over for good.

Be open with your friend about the new relationship. As awkward as telling your friend about your new girlfriend may be, it is far preferable to having him discover the two of you by surprise in one of his and her favorite places. If you're serious about the relationship, you need to be as open about it as possible. You may even receive his blessing, since he knows she'll be in the company of someone he knows and trusts. If the break-up was amicable, then there is always the possibility the three of you can become closer as friends. You probably don't want to spend all of your time discussing your "new" girlfriend with her ex, but at least you won't be tap dancing around the subject if he brings it up in conversation.

Avoid using your friend as Dear Abby. Your friend may be comfortable with you dating his ex, but try not to push it. Your girlfriend is not a used car, so don't spend your time talking with the former "owner" about its pluses and minuses. Any problems you may be having as a couple are your problems, not the ex-boyfriend's. If he chooses to share some personal anecdotes about their time together that's his decision, but you shouldn't try to solicit advice just because he's familiar with the topic at hand. Conversely, whatever issues lead up to their break-up are their business, not necessarily yours. Sometimes you may find yourself talking candidly with your best friend about women, but other times you'll be talking with her ex-boyfriend, who may or may not be interested in all the details. Treat any information you may want to solicit from her ex-boyfriend as a "Break Glass in Case of Emergency" situation.

Make your friend as comfortable as possible around both of you. If he has truly moved on and is currently dating someone, you may want to suggest a double date to break the tension. If the former couple has an opportunity to see each other in healthy, committed relationship, it could help the healing process. You may want to avoid having such informal get-togethers in places significant to your friend and his ex, however. Out of respect for your friendship, you need to be sensitive about public displays of affection. You may want to plan specific times for a guy's night out to let your friend know you haven't abandoned the friendship entirely.

Dating a friend's ex-girlfriend can be a delicate operation at first, but if everyone involved remains open and mature about the new arrangement, it should get easier. Everybody handles former relationships differently, so you may find yourself temporarily at odds with your friend or you may be pleasantly surprised at his acceptance of the situation. Either way, if you handle your end of the relationship with sensitivity toward's your friend's feelings, you should be able to overcome the initial awkwardness and have a satisfying romantic relationship and a strong friendship at the same time.