I'm really into this guy who's in my master's program. He's good looking and seems to be into me. We run into each other all the time on campus, and I always catch him looking at me. Though we haven't actually had a small seminar together yet, I am pretty sure he's in the same program. The only problem is we have never actually spoken! I am really shy and have close to no experience pursuing men. Could you give me some tips on how to approach him in a subtle way? I want to make contact without coming off as a crazy stalker.
— Crushing Like Crazy Catherine
To see DearSugar's answer,
Dear Crushing Like Crazy Catherine,
You may be shy, but it takes some guts to decide to make a move on someone! If this is your first experience being the pursuer, then I think subtle is better both for him and you. But being more subtle is going to take patience and time. First of all, make sure he knows that you've noticed him. Next time you catch him looking at you, hold his gaze for a moment and offer a quick smile. Once you've done this a few times, there will be enough recognition between the two of you that when you see him around campus, you can comfortably give a wave or exchange a "hello."
After you've seen each other enough with a more legitimate acknowledgment, a quick conversation will only be natural. It doesn't have to be serious or even that informative to let him know that you're interested in talking. Once you guys have had your first conversation, more are sure to follow so go ahead and start revealing a little bit about yourself and learning more about him. Before long, you might find it not so scary to go ahead and ask him out; then again, he might beat you to the punch!