I’m a 29-year-old man. I became friends with a female co-worker at my relatively new teaching job, and she seems to enjoy talking to me and spending time with me. In fact, we have been out one-on-one a few times, and have another outing planned for this weekend. I guess I should be very happy, but I am concerned because she is very hard to read. On the last date, I paid for her lunch, which she thanked me for. Sometimes after the school day ends, I have been stopping by her classroom, and we’ve been talking for up to an hour each time. I know she likes me; that’s not the issue. The issue is that I don’t know to what extent she likes me. We have a lot in common, and every time I talk to her I find out something else about her that I like.

I realized a few weeks ago that I love her. Yes, my feelings are strong enough to use the word “love.” She is a bit younger and has never been in a relationship before. I can’t tell if she is attracted to me and is just very subdued about showing it, or if she just thinks of me as a friend. Surely she must have picked up by now that I am interested in her, seeing how I paid for her lunch the last time and often invite her to do things one-on-one. I am reaching the point where I am tired of trying to guess and want to know once and for all if she returns my feelings. I’m also trying to be very careful in my interactions with her and take it slow. I have not been in a relationship in a very long time, and my last girlfriend hurt me terribly when she broke up with me.

More or less, I have an anxiety disorder, and she couldn’t handle it. I swore that I would never let anyone hurt me like that again. My feelings of distrust have gotten a lot better in the last couple of years, but I can feel my cynicism kicking in as I prepare for this weekend. I fear my coworker might use it as an opportunity to tell me that she just wants to be friends, in which case I would most likely give up on relationships altogether and accept my life as a bachelor. I would be hurt that much. In fact, I am beginning to suspect that she is not attracted to me and just enjoys seeing the area with someone who knows it, since she is from out of state. I don’t want to be subdued, angry, or moody this weekend, since I have been looking forward to our outing for some time. I still don’t know if it’s even a date in her eyes, and I don’t know how to go about finding out how she feels. I have talked to my therapist about it, and he told me that he was glad I was taking it slow, and that I would know when the time was right to move on to the next stage in our friendship. I feel like that time is either this weekend or soon thereafter, but I don’t know how to deal with the situation.

– Next stage