How can I ask him if he's doing alright?

[Anonymous]

A friend of mine that I like has been acting different recently. I know he used to be really interested in me, so initially I thought he was acting different because he wasn't interested in me anymore. In general he's just been more distant and kind of gloomy lately, where typically he's a very happy, outgoing person. It may be the case that he doesn't like me anymore, but I've also been starting to think he actually has something going on in his personal life right now that's bringing him down, because he seems like he's in a rut. I think I have an idea of what is bothering him, so I would like to ask him how he's doing, but I'm not really sure how to ask. He's also the kind of person who will just say he's fine, even if he's not. I need an opportunity to ask him how he's doing, but we don't hang out anymore these days because he always says he's broke (which is actually true and I think is one of the things bothering him). I would also like to do something nice for him, but I already took him out to dinner a few weeks ago to celebrate something, and I don't want to become someone who just pays for everything every time we go out together. I've been thinking about maybe making him some food since he lives on his own and he's short on money...But I really want to do this as a friend, not someone who's interested in him. In short, I want to ask him about what's been bothering him and I want to do something nice to help him get out of this rut that he's been in, but I want to do it as just a friend because I'm not sure he likes me anymore and I don't want to make him uncomfortable if that's the case. When you're going through a hard time, what are some things your friends do for you that help you get out of your rut?

[XRabbitHeartX]

Do you know what his favorite foods are? Does he have a sweet tooth? You can always make something as you suggested and then ask him to come over mentioning you made his favorite food. This will sort of make him have to say yes in a sneaky way. Once he's there you can bring this up. If he says he's just fine, then tell him you're not going to fall for it and that you really care about him and want to know what's going on. Even IF he likes you, there's nothing wrong with showing someone you care about them. Love and mushy things aside it's friendly and very kind of you regardless of who likes you or who has feelings. If he for some reason mistakes your behavior and think you are doing this because you like him, it's totally on him and not on you. You know in your heart what your intentions are and that's all that matters. I think it's very sweet of you to care for him like that and I'm sure he'll also appreciate someone caring about him.

As for your last question, when I'm down I always try to hang out with my friends. It helps to take my mind off things and talking about it always makes me feel better too. So I guess hanging out and spending time with me are things my friends will do. Usually though I initiate it cause I'm quite good at hiding my emotions so I need to often reach out to others instead of expecting them to do something.

[Asker]

Thank you for your answer! The problem is actually that I'm the one interested in him and I don't think he's interested in me anymore, but we both talked about our feelings in the past so he knows I like him...So I worry that if he doesn't like me anymore, he may be uncomfortable hanging out with me because he thinks I'm reading into our relationship or something, when really even though I do like him, right now I just want to make sure he's doing alright, as a friend.

[XRabbitHeartX]

Even if he doesn't have romantic feelings for you, it still stays nice to have someone care about you. I'd still do it without worrying about how he'll read into things. You know how it is and that's all that matters. If he wants to assume things, let him :)

[kovalinkie19]

Well you can listen to his problems, you can hangout with him, you can watch a TV show or film he likes with him, you can give him a hug if he's that kind of guy, you can do something else if you think he'd appreciate you showing that means a lot to you, etc...

If you like him as more than a friend and you think he still has feelings, then you could give him a kiss or something.

Just think little things.

[serp777]

"he lives on his own and he's short on money" and the girl that he really liked isn't interested in anything other than a platonic relationship. Sounds like a few decent reasons to be depressed.

[Asker]

He lives on his own as in he supports himself...he has roommates. Also, I AM interested in being more than just friends, but recently he's been giving me the impression that he's no longer interested.

[Anonymous]

let him sort out his own problems, he probably doesn't need your help.