Q: I read your article on “Dating: How Far Can I Go To Encourage a Relationship without seeming desperate?” and had to see your opinion on a situation. I’ve had an infatuation with this guy I know for almost 6 years. We were both 18 and 19 at the time when we first met, and I tried to pursue him at the time but failed miserably. I gave up around that time pursuing him, but always admired him. I ran into him randomly 3 years later when I was 21, and my infatuation began again. We have a lot of things in common, and have many mutual friends, but never actually hung out at all, whatsoever. I consider myself a shy person so I never had the guts to confront him about my feelings but would do subtle things like comment or like his posts on social networks. Two years ago we kind of began talking a little because I work in a field he is interested in (he initiated it). We talked very on and off for a few months and ran into each other in person at the bar but since I am a shy girl I would be very nervous in front of him and be very quiet. When he does see me, he does always initiate talking to me and for the most part during this time he initiated the conversations online. He fell of the face of the earth for around a year and a half. This past year (which is 6 years since we first met) I decided to subtly hint that I still had a crush again (online only). If I’d see job opportunities that would interest him I message him about it, also his father died this past year and I sent him a private message with my condolences, but in regards to speaking further nothing else. We coincidentally work a block away from each other at work, and I ran into him a few months back and he said we should grab lunch. He never pursued anything, which was a blow. I’ve dated on and off throughout these 6 years, but can’t seem to ever get over this guy. I consider myself to be an attractive and confident woman, but with him I get so nervous. We have a lot of mutual friends, and several of them have tried to pursue me which makes things awkward. Despite the fact that we have these mutual friends, we have never hung out other than running into each other here and there. He was dating a girl on and off during this time, but I know he is currently single. I sent him a message with a job opportunity a month ago, more as an effort to get his attention about the lunch but he didn’t mention it, and just was thankful for me sending the link. After all this time I have been unable to get over him, and am at a loss for what to do. Please help.
A: I think you should ask him out to lunch at a particular restaurant on a particular date. You can say that they have a particularly good dish of whatever and you would like his opinion about it–or say something else. All you can do is encourage him. You cannot do more; and I get the feeling you haven’t done that much. You are supposed to indicate to him that you like him (not by saying I “I like you,” which usually suggests something else; but by suggesting particular things you can do together. You cannot go further than that. By the way, something is going wrong if you have not found anyone else interesting to you in all this time.
– Dr. Neuman