1. If nothing else comes of it, if you don’t end up in a real relationship with him, will you still be happy you slept with him? If not, then you should reconsider.
2. Will it complicate your life? You don’t want to fuck a coworker and lose your job or fuck your bestie’s boyfriend and lose a friendship.
3. Why do you want to fuck him? If the answer is to make your ex jealous or to make yourself feel sexy again, there are better ways to do it.
4. Are you going to run into him all the time? If you’re taking the same class or working in the same office, then you probably don’t want to fuck him.
5. Can you keep emotions out of the equation? If you’re going to be having a one-night stand or starting a FWB situation, ask yourself if you can handle it.
6. Are you going to regret it after it happens? Right now, your hormones might be tricking you into thinking you need to bang him ASAP. But try to think with your head and not just your pussy.
7. Does he have any STDs? I know it’s an awkward conversation, but it’s even more awkward to tell your next hookup that you have herpes.
8. Is he single? It can’t hurt to do a little digging. At least check his Facebook to see what his relationship status is set to.
9. Do you actually have a place to do it? You don’t want to end up having a quickie in a random bathroom stall, just because both of your dorms are occupied.
10. Do you have any condoms? You can’t expect him to pick them up, so make sure you have a few in your bag if you’re serious about the hookup.
11. Do you mind losing him? You might be friends now, but after it’s over, that friendship could end. Make sure you’re prepared for that possibility.
12. Have you shaved? You don’t have to get a Brazilian, but you should make sure it’s tidy down there.
13. Have you been tested recently? You don’t want him to get anything from you. You could ruin his life and your reputation.
14. Do you know him well enough? As in, do you know he’s not a serial killer. You don’t want to end up alone in his apartment if he’s planning on taking advantage of you.
15. Have you showered? If not, you better get to it.
16. Does he seem like the type of guy to give more than take? I mean, if you aren’t going to get an orgasm out of the deal, why bother?
17. Do you know what he wants from you? If he wants one night of wild sex and you want a legitimate relationship, you should probably rethink the hookup.
18. Do you know what you want from him? Sex can complicate things, so try to figure out how you feel about him before he sticks it in.
19. Is masturbating a better idea? If you know nothing good will come of fucking him, you can always fantasize about him while fucking yourself.