The decision to flirt with or date a friend’s ex is fairly complicated. It depends on how long they dated, how the friend feels about them now, how close you are to your friend, and how strongly you feel for the ex.

I’ve written my answers to these scenarios below.

When you’re the one with the crush:

A crush can be a difficult thing to live with. When you really like someone and keep hoping they will ask you out it can hurt to think that one of your friends would even consider going on a date with them. However, I think it is time to put the crush in a different perspective. If you aren’t being asked out by the person you like (or they aren’t telling you that they want to spend more time with you) than they are probably not interested in you romantically. That totally hurts and is a bummer but the truth can also lead to healing and get you back on track for a real relationship rather than a dead-end crush. It might hurt to see your friend flirt with or date the person, but the mature thing is to find a way to be happy for them. You don’t own either of them and are not entitled to keeping two people apart just because you have a crush. If you need to step back from the friendship for a while because it is too hard that is understandable but be fair and upfront about your feelings. For example, if you feel that you have shared too much with your friend about the crush and your friend dating your crush would hurt too much than be honest but also ask them how strongly they feel for the person and if the other person seems to be reciprocating. If your friend is only casually interested in your crush or is uncertain that your crush is interested in them than ask them not to flirt with or date them since the likelihood of the relationship going anywhere is low and it might distance your friendship. If your friend and crush is very interested in each other and they really might be a good fit for one another express how hard it is and that you may need to be a little distant for a while but that you understand and just want them both to be happy.

 When you are the roommate or friend of someone with a crush:

Remember that respect is essential to all friendships. If you want to preserve a friendship than talk with your friends or roommates about how you want to handle it when both of you like the same person. Discussing this situation in advance can help you avoid awkward situations or hurt feelings later. Consider using a rating scale from 1 to 10. If one of you likes the person the most (such as a 7 or higher) the other would back off. If you are both only somewhat interested (such as a 5) than both of you can go for it because neither is too into him/her. In this way you can talk about the degree to which it is important to you and how you want to respect each other’s feelings. You may also want to agree to not flirt with the person in front of the other person so as to not create feelings of jealousy or competition.

 When you or your friend has gone on a few dates with them:

Going on a few dates does not a relationship make so expecting that friends shouldn’t date the person after you stop dating is a bit unrealistic and immature. That being said, it would also be tacky of a friend to flirt or pursue someone immediately after you stop seeing them. Waiting even a month or two would be best. It would also be wise to ask a close friend how they feel about it before proceeding forward. Some people won’t have a problem with it at all, especially if they were never very interested. Again, communication and understanding what the other person meant to them is key to showing respect.

 When you or your friend were in a serious relationship with them:

Once someone has been in a committed relationship everything changes a bit, especially if it was a long-term relationship or marriage. Asking out a friend’s ex is almost a certain way to end a friendship (especially if the friend wasn’t the one who wanted the relationship to end). It isn’t always this way, but most of the time a friend won’t be able to see the two of you together without feeling crushed. If the friend confided in you during the break up they will feel even more betrayed (especially if you encouraged the break up). If you wait six months to a year (or until they are in a new relationship) you might find them to be more understanding but it is still tricky. If you ask how they feel about the idea of you dating their ex before you do it they’ll at least feel that you cared enough to ask first. This might help the friendship to recover from the shock of you dating their ex, but you take a risk of losing the friendship. Of course, if they were the ones who wanted the break up or were never that into their ex they might not have an issue with it. I guess the decision to date an ex really depends on how deeply you care about the friendship and how much you want it to continue. Some singles will rationalize that once they are married they won’t spend much time with their friends anyway, whereas other singles will point out that most relationships don’t end in marriage so why take the chance of losing a friend for a temporary fling. Again the best practice is to talk about it first with your friend so you can sense how big of a violation this might be to them.

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