10 Questions to Ask Yourself Before You Decide To Date a Friend's Ex

If you haven’t noticed, there are some who feel strongly that if the couple isn’t married, there are no boundaries, and even these days the level of respect for marriage has waned in some instances. But if you know you were giving them the eye or even took things further while your friend was still in a relationship with this person, you were wrong from the start and it’s most likely going nowhere fast.

There are times when someone will become attracted to a friend’s ex years after the relationship. Is this a childhood friend or someone you consider a best friend or sister? Would you be devastated if she never spoke to you again? If the answer is, “we were just acquaintances and didn’t talk regularly” and you know it really wouldn’t bother you if the friendship was severed then we would recommend that you have a conversation with her just for “good faith” and then proceed. But if you’ve always been close, is this man even worth it?

Is your friend happy in her new relationship and has long moved on? If this ex was someone that was a fling, a relatively short-term relationship and not the former love of her life, we would say proceed and see where things go...

Sometimes when there’s unfinished business and both are still single, dating the ex will just make things messy all around but if they have tried every way from Sunday and both eventually said, I’m over it, the ex could be fair game. Can you imagine if one of them is thinking in the back of their mind that they would be open to trying again if their current circumstances were different, i.e. if they only were in the same location or if ever one of them broke up with their current partner. A good question to ask is how did the relationship end and would either of them ever be open to trying again? A tough question but you really need to know the answer.

If you were the unbiased party that both parties trusted when they were together or you were her listening ear and heard all of the wonderful things about him as well as the troubles in the relationship, you probably don’t want to touch that. The reason is, she is going to accuse you or feel as if you had another agenda the entire time. Steer clear of him…..it’s not worth it because she will most likely never trust you again...even if you were innocent at the time.

Let’s face it there are casual relationships that never materialized and then there’s always that main “one” that got away or just didn’t work out but the feelings and respect for each other was always over the top. If you know there were deep seeded feelings and the person is still on a pedestal in your friend’s eyes, we would say it’s really not worth pursuing. Ask about his friends…

Was this a casual 3 month stint or was this something where years and years were invested? As a rule of thumb anything under 6 months is most likely open for discussion but 6 months plus requires more thought and consideration of whether it’s even worth opening this can of worms.

Again if it was casual intimacy on both parts, it may not be an issue but it’s quite possible that even if it started as a casual physical relationship, quite often over time one person started to develop feelings even if the other didn’t. So tread forward with caution if they both say it was just a fling but if one person seems hesitant, leave it alone.

Yikes! This is tricky and we’ve seen this suspense, drama, thriller movie play out especially when it’s new, fun, and forbidden. Often times, it doesn’t end well however unless you have both of their blessings, which is rare.

Yes you may have had a really great friend in high school or college but over the years you lost touch. Their ex may be an option depending on how you met them. However if you’re still hanging often with the friend and this person will be reintroduced to the same circle, it might not be worth the uncomfortable times that lie ahead with everyone involved.

Overall, we agree it is a case-by-case situation and you should tread lightly. We know there often seems like there is a shortage of great guys out there but that’s not a reason to double up on the same man unless it’s an unbelievable opportunity that lies ahead.  It’s always best to have a conversation as adults and gauge your friends feelings very early on.  We’re not saying that she has the deciding vote whether you proceed or not but we can tell you that by not having the conversation with her, your relationship with your girlfriend can go left quickly and you may have lost a friend you’ve had a lot longer than this relationship may last. Ask yourself, is it worth the risk? 

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