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When you're single, finding somebody that you connect with is like finding the Holy Grail. It's rare, it's precious, and you don't want to give it up unless you absolutely have to. For many people one "absolutely have to" situation is when the Holy Grail in question is your best friend's ex. In general, ex's are considered off limits if you want to keep your friendship... not to mention that not dating a friend's ex is a good way to avoid a lot of potential drama.

That said, there are times when dating your best friend's ex seems irresistible. If the opportunity arises to develop a romantic relationship with the ex of a good friend and you just can't bring yourself to say no (or don't feel you should have to), it might be okay to move forward. Just be sure to do it with caution, and be sure to do it right.

1. Gauge Your Friend's Feelings

Generally, the main goal when dating a friend's ex (besides, of course, having a romantic relationship) is maintaining a healthy friendship with your friend. The easiest way to ruin this is to date somebody your friend still has feelings for. Before even approaching your friend about your feelings for his or her ex, be sure you have a good idea of your friend's feelings. Was it a messy break-up, and they're still nursing their wounds? Have they spoken recently about still missing or loving their ex? Were they unceremoniously dumped and still feeling raw and hurt? Then beginning something with their ex is a good way to bring your friendship to an end. Go with great caution.

2. Be Sure Your Feelings are Reciprocated

If you have feelings for your best friend's ex, you want to be sure the feeling is mutual before you make a move. After all, if the ex isn't interested in you romantically, what's the point of hurting your best friend by asking about dating them? Don't put yourself in an uncomfortable situation unless you're positive it's worth it.

3, 4, and 5. Be Upfront, Be Upfront, Be Upfront!

No, I can't say it enough, which is why it gets three spaces all to itself. The very worst thing you can do for your friendship is allowing your friend to hear through the grapevine about your relationship with their ex. If you're considering starting something up with your friend's ex, speak to your friend before you do a thing. Ask for their honest feedback, and actually listen. Don't just wait for your friend to tell you what you want to hear; instead, show that you really care how they feel. If necessary, give them time to think before giving you an answer.

6. Decide How Strong Your Friendship is

Did your friend give you the go-ahead? That doesn't necessarily mean you're in the all-clear. In almost every situation, dating a friend's ex is going to put an emotional strain on your friendship. Before you decide to go ahead with it, you need to be sure your friendship can withstand the pressure. If not, you may be giving up your friend without intending to... even if you do get a green light.

7. Get Feedback at the Beginning

When your best friend gives you the all-clear to date their ex, it doesn't necessarily mean that the idea doesn't bother them-- even if they say it's just fine. It may happen that you friend thinks that seeing you with their ex won't be painful, but balks when it turns out to be hurtful. If your friendship is more important to you than this new romantic relationship, make sure to ask your friend once or twice how they're feeling about the relationship as it moves forward.

8. Be Open, but Restrained

When you're dating your best friend's ex, one of the most difficult things can be striking a balance between being totally open and maintaining some space. You best friend probably doesn't want to spend all their free time with an ex-boyfriend or -girlfriend. But neither do you want to behave as if your relationship is a shameful secret. Be sure your friend knows that you're perfectly happy to share and talk about your relationship. Never flaunt it unless you want to foster resentment instead of friendship.

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