Hey lexy99,

I have the same issues. I’ve been single for something like 7 years; last time I went on a date was probably 3 or 4 years ago. I’m still trying the online thing, but it seems the women that are interested in me are not women I’d be interested in, and vice versa. But the few times that it came to “where do we go from here” (i.e. “do you want to meet?”) I’ve felt the anxiety and written things like “just interested in discussing things” or something.

I wrote that because I was doing what you describe: what-iffing. What if I hate her personality? What if I *like* her personality, and then I have to change my whole life to accommodate a relationship?

Your what-ifs all seem to go down a fearful road. It may take some work, but can you replace the fearful what-ifs with positive thoughts about dating, even if you don’t believe the positive thoughts? Stuff maybe like “Ok, I just arranged a date, it makes sense that I’m afraid, but I can do this anyway, and I may even have a good time. At least I will have gone on a date. I can do this!”? Breathing exercises can help as well. Perhaps breathe deeply and think to yourself “I am strong. I can do this”? Making this part of a daily routine can really help; 2 months ago I was a disaster of hurtful emotions, and practicing what I just described as well as being in the moment helped tremendously…I still practice the breathing every night before bed. It’s easier now that it’s become routine.

If you do like him, you can still take it slow if you want to. But I suggest that, when you make a date, you do your best to focus on the fact that you’ve accomplished making one date as opposed to worrying about what might happen afterward. From your words, it sounds like worrying is what you do and what you’re used to. When the worry thoughts come in (“what if I don’t like him, what if I do?”), try to let them roll or slide away from you. Maybe visualize the thoughts evaporating, and then replacing the thoughts with either being in the moment or with positive thoughts like “I can deal with that when or if it happens”.

If you don’t like him, you can be polite at the date, and be assertive later (perhaps online) about how you don’t think it’s going to work out. If he brings it up mid-date, maybe say something like “I’m not sure how I feel about this. I need time to think about it” and get back to him later.

Are you asking about dating more than one person because there’s currently more than one guy you want to date? Given the anxiety you have about one date, I’d take it slow and schedule one date. But if you want to do two dates, I think that’s fine; a date is not a relationship, you’re not beholden to anyone else.

Hope this helps.