Maybe you never noticed them before. Or maybe you did, and now they’re available. The only problem is the reason they weren’t available before is that they were dating your friend.
You care; you really do. But you can’t help but think that maybe, just maybe, this is meant to be. That the timing is right. That you shouldn’t have to pass them by just because it didn’t work out between your friend and them.
Or should you?
Deciding whether to date your friend’s ex is never an easy decision to make. But, pretty much regardless of what you choose to do, someone’s not going to get what they want, or worse still, someone’s going to get hurt. So what’s a single guy or girl to do?
Ask yourself the following questions, of course. So you can make a decision — an informed one.
1. What was the reason for the breakup?
Do you know why your friend’s relationship ended? The reason could make a difference. For instance, if your friend was betrayed, if their ex cheated on them, you dating the ex could be seen by your friend as an extension of that same betrayal.
Not to mention, if this person has a history of cheating on the people they date, even if it’s seemingly harmless activity such as micro-cheating, do you really want to be the one having to figure out if there’s anything to these minor indiscretions? Living on the edge in a relationship is no fun and will likely only lead you to the same fate as your friend, which brings me to my next point.
2. Is there a chance your relationship could end the same way?
If you think there’s a distinct possibility based on past behavior, current behavior, and whatever other red flags you can spot, tread lightly. The apple of your eye may, in fact, be rotten. Or, at a minimum, not ready to be picked. In which case, perhaps you should consider finding a different one.
For example, if your friend’s relationship ended because of cheating, you may want to think twice. Though the adage once a cheater, always a cheater isn’t necessarily true, you should take a step back and look at the situation for what it is. And whether you want to take the risk history won’t repeat itself.
The same holds for any other reasons why the relationship ended, including whether they treated your friend poorly, didn’t want to pay on dates, or displayed evidence of being a narcissist or someone with borderline personality disorder.
3. How long ago was the breakup?
You know how people say it’s all about timing in matters of the heart? Well, how long ago a person went through a breakup does matter. Not just because the person you have your heart set on might not be over the person they were dating. But because if you know the person they were dating, are friends with them, they could see you not only you dating their ex as a betrayal to them as I stated earlier, but, depending on how recent the breakup was, as a catalyst in their relationship’s demise. Neither of these situations bode well for you.
With the first, you could be a rebound for them, which may mean your relationship will never go the distance and become a source of heartache for you because the other person’s heart and head will be somewhere else. As for the latter reason, do you want your friend to think you had anything to do with their breakup? Which brings me to my next question: Did you?
Better to own your truth now than try and defend your actions later, after the damage has been done. To your friend and in the court of public opinion.
4. Is your friend over their ex?
Now, if you know for sure your friend is over the ex, then most of the previous situations don’t apply to you or matter. But how do you know your friend is over their ex? Don’t rely on time alone here. As we know, it can take a long time to get over a past relationship. The best way to find out is to ask your friend if they’re over their ex and if they would care if you dated them.
While you don’t want to ask your friend for their permission, you should be prepared that your friend might take offense that you’re even asking and, even more so, at the thought of you dating someone they were once involved with. You need to be prepared for that possibility and what you will say to your friend. Much of that will come down to how you answer this next question.
5. What is your motivation for dating your friend’s ex?
This is the part where you have to get real with yourself. Why are you thinking about dating this person? Are you genuinely interested in them? Or is there another reason you want to date this person now, like are you trying to, for whatever reason, incite your friend?
Depending on your feelings, you need to clarify with yourself whether you would be willing to give them up for the sake of preserving your friendship because, depending on what your friend says, you may have to. If what your friend says matters to you, that is.
6. Is it important to you to have your friend’s blessing?
Don’t just ask yourself how good a friend your friend is to you, but also how good a friend you are and want to be to them. Compare this question to the times when you ask someone in need, “Can I help?”
Many times when people ask this question to others, they aren’t expecting the person to take them up on their offer. If it’s important to have your friend’s blessing, prepare yourself that they may actually ask you to step away from dating their ex. In other words, if you’re asking for your friend’s blessing, understand there’s a chance they may not give it to you.
7. Is it worth losing a friend over if you don’t?
If you don’t get the blessing you’re looking for, this is the time you must decide what you stand to gain and what you stand to lose, and which is worth more to you. There’s no guarantee either way. The only thing you can count on is that the decision won’t be easy.