Say, for instance, that you know that continuing to hook up with your guy without a commitment will make you anxious. If this guy can't give you a relationship that makes you feel happy and secure, then you're better off not continuing things. Now you need to make it clear that your feelings have shifted. Just telling him as it is—that you went into this totally attracted to him and you didn't have any expectations.
But for the past [amount of time here] you've started to feel more strongly for him and want to know where he stands. After you've let him know how you feel, suggest another time to meet up and chat (ideally, he'll have feelings too and this will be your "first date." Worst case, you can meet casually and have a discussion about moving on and respecting each other's decision—not the end of the world).
Especially if there's a hobby you both enjoy.__Let the rest happen naturally.__Now that you've laid it all out there, take the pressure off yourself. If he doesn't want to move things forward, or doesn't make any plans, you've just dodged a bullet and saved yourself more hurt feelings in the future. Any other suggestions for how to make this transition less terrifying?
Have you ever tried to turn a hookup into a relationship (and were you successful)?
DOWN We all have sent or accepted a friend request because of a nagging crush.
While poking them feels a little too forward and directly messaging them carries unnecessary anxiety, DOWN lets you connect with your crush anonymously.
For example, I thought I would be a lawyer, but I hate arguing and feel bad when someone else loses—a whole other issue.