Double the Trouble: What to Do When You're Hooking Up With More Than One Guy

What if I want more?
If you want to take things to the next level with one of your guys, tell him, but be prepared for an answer you may not like. Despite any double standards, and despite any of your reasons for participating in an ongoing casual hook-up, you should not string yourself along or allow him to string you along. Shield advises saying something like, “I really like being with you, and I’d like to spend more time with you if you’re open to that.”
If it turns out this guy wants to spend more time with you, too, make sure to break it off with the other guy or guys in your life (or, more specifically, in your bed). If you didn’t, you would be venturing into cheating territory, and that’s not good for anyone.

What if he wants more and I’m not interested?
Remember the golden rule: do unto others as you would have them do unto you.
If you entered the hook-up with this guy to have fun rather than to become emotionally involved, don’t get sucked into the drama of pretending to care about him. “There’s not much worse than lying to him,” says Danai.
“If you don’t want a relationship, say, ‘I enjoy having a sexual relationship. That’s what we agreed on, and I’m not really looking for a serious commitment at this time,’” says Shield.
Your best option may be to just make a clean break and find a new guy. This guy’s feelings will most likely not go away as you continue to hook up, so you’d be doing him and yourself a favor by just ending it.

How do I let him know there is more than one guy?
If you don’t care to keep things a secret – scratch that, actively don’t want to keep things secret – then be straightforward with all of the guys. Before the next time you hook up, say something along the lines of, “I’ve been having a really great time with you, but I’m not looking for anything exclusive right now. Are you feeling the same way?”
Realize that you’re running the risk of him declining any future hook-ups. But if that’s the case, you’re doing him a favor by letting him know now rather than having him find out later and getting upset.