I’m not sure where this is going...

Illustration/Uday Mohite

I have been meeting this guy for dinner or a movie for months, and it feels like a game because I can't figure out what's going on. I know he likes me because he wouldn't keep asking me out if he didn't, but he never says anything specific about where this is going. I have told him I like him a lot and he knows I am looking for a relationship, but it is awkward for me to bring it up again if he doesn't even give me a sign of how he feels. I am embarrassed about mentioning the topic again but if I don't say anything, this can't continue the way it has. I don't want to meet him for dinner just because he asks me out. Should I stop seeing him and wait until he is specific about his feelings?
Insisting on a conversation about this may be worthwhile because it helps you avoid wasting any more time. If he doesn't want to give you an honest response, you know there is no point. He may ask for more time if he isn't sure about this, but that request needs to come from him, and he needs to explain why he needs time too, because he owes you that much.

My partner left me a few months ago but I know he did this because he has been suffering from depression. Our relationship was strained, but not because we didn't love each other. I tried my best to hold on to him, but he knew it wouldn't work because he couldn't cope with day-to-day stuff. I am worried about him and want him back because I believe my presence was good for him. How do I make him understand this?
If he isn't getting any professional help, you may not be able to get through to him. If he is, there may come a time when he sees what your presence means. Until then, all you can do is wait and let him know that.

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