To make a move, or not – I guess that’s ultimately my question. I have gotten to know a guy over the last year or so and I find myself stuck in a state of limbo over whether I should attempt to clarify the parameters of our relationship. Background info: We are both early 30s, single, and established in our careers. We met at a professional event and now see each other at group outings and activities. While at these group activities, we tend to gravitate to each other. We began communicating regularly through email and text, discovering we have lots in common. A few months ago I asked him to get together outside of this group setting, and we have done so a few times. However, I feel like there is still this murkiness surrounding the interest level on his part. I feel like I have given him some pretty clear signals that I would be open to being more than friends, but perhaps I’m wrong.

Friends have been pressuring me to make a direct move, but I have been hesitant to do so – mainly because I do enjoy being friends and would hate to ruin that, but also because of our shared professional connections. (FYI: We don’t actually work together.) Not to mention rejection sucks.

Female friends keep telling me that with guys you have to basically spell it out in black and white; guys are less likely to “read between the lines” or take a hint, and I will never know what he is thinking unless I take a risk and be direct. Male friends keep telling me that no guy wastes this much time on a girl he isn’t at least somewhat interested in. Friends who have hung out with both of us tell me there is an obvious connection and mutual interest going on.

Recently, I pressed him a little on what his motivation for coming to group activities was, hoping it might spur him to open up a little. Instead, his answers were vague and he seemed almost spooked by my asking. So now my friends are telling me I have two options: 1) let it go and let the chips fall where they may or 2) double down and just ask him out and get it over with, preparing for the likelihood of rejection and the damage of a platonic relationship. I can’t help but return to the idea that if he was really interested, he would have made it clear by now.

I have also always been friends with a lot of guys, so I find it increasingly difficult to identify the friendzone line. I assume guys just want me as a pal. So do I let it go or make a move?

– Forever Friendzoned