For the purpose of this post, I’m going to assume that you and your ex have been apart for quite some time now. Maybe months, maybe years – either way, the relationship is finished, over and done. Nobody still has any soft feelings and you are both committed to never being together ever again.

Good. Glad we got that out of the way.

Now, when it comes to dating a mutual friend you shared with your ex, this territory can be tricky and it can prompt some pretty confused feelings from your former flame. That said, you are free to date whom you choose and as long as this person was more your friend from the beginning then we’re going to go ahead and say that you’re in the clear date them, make out, and even have sex with them.

Here are few things you need to consider before you start bedding that buddy you always had a secret crush on:

Are they down?

Sure, you might actively pursue this particular person or perhaps you’ve always exchanged flirtatious banter, but the real question is how are they responding to it now that you’re no longer with your ex? If you get the feeling that they’re shuddering away then it’s probably not a good idea. However, if they are actively responding to your come-ons, then you might want to talk about whether they feel comfortable fooling around with you with the knowledge that they might still hang with your ex from time to time.

How did you meet them?

When breakups happen, the division of friends follows this basic rule: Whoever was your friend first stays on your side and vice versa. Anyone you met along the way during the relationship is pretty much free territory. If you were closer with this person whom you now desire, then they are yours for the taking. However, if they became really close with your ex, then you might want to steer clear as this episode could make your ex hate you forever and forever. If you don’t care that’s fine.

What is your motivation?

Do you genuinely like this person? Or are you using them to make your ex jealous? You really need to analyze your motives, and question your intent. In the post breakup phase, it’s easy to have a lot of confused thoughts and run to the person you’ve always had a minor crush on out of desperation. You really have to be over your ex in order to start dating anyone again (this includes strangers and mutual friends). Anything too soon could result in the same patterns as you have had no time for self-improvement and reflection.