How can I help him?

Chat at 1 p.m.

I met a guy about four months ago on a dating app. We're both in our late 30s. It was instant chemistry – he was personable, funny, and easy to talk to. Our first date was great! Lots of laughing, sharing stories, no awkward silences, and ended with an awesome chemistry-filled kiss. We would text and talk almost every day, and opened up to each other about some serious topics in our lives. Nothing was ever awkward; it was always comfortable and easy. We made plans for the coming year including future trips, and were already talking about dates well into the summer. Cut to about a month ago. We started having deep conversations about our relationship almost twice a week. His low self-esteem/re-discovered depression started rearing its ugly head. He would constantly say that he was "useless," not worth my time, and that he didn't know why I liked him. He blatantly said that "this will end badly, because everything in my life ends badly, and it's always my fault." I would always beg to differ – truthfully, and not just to placate him – but it started getting really dark.

I would do everything I could to counter those statements, and try to prove to him that he was totally worth my time, as well as my (or anyone's!) affection. I admit it was draining on my part, but I pushed through. I had seen him when he wasn't in a bad place, and he is an awesome guy with a lot to offer. I wanted to help him get through this dark period (the winter and the holidays can be so cruel!), and show him that it was and will be worth it. But that wasn't to be. About 2 weeks ago, he told me to stop trying. He said it made him feel worse when I'd ask him to do something or make plans, because he never feels like doing anything or being around anyone anymore; constantly saying no was making him realize that I deserve better. I respect his request, though I'm sad. I'm not even hurt by it, because I understand that he's in a dark place, and if he wasn't depressed we'd likely be together. My question is: How can I help him? Can I even help him? We met because we were dating, but this goes beyond holding out hope for a relationship. This is a genuine concern. He did tell me he was seeing a therapist that he liked, so I'm hopeful that has continued and will continue. But is there a way that I can try and make him understand that I care about him in all senses of the word, and not just in the relationship sense? That I will always be around to support, assist, help, listen, etc.? Or is it too far gone, and I have to just let it be? Any suggestions would be great.

- Help

Before you tell this man that you'll be there for him no matter what, you should think about your own self-care. You wanted a romantic relationship with this person, but you're not going to get it. It's true that you don't have to cope with the bad feelings that come with rejection, but you are experiencing a loss. I don't want you to have to push those feelings aside because of this other person's needs.

It would be nice for you to be able to truly move on. I mean, would you feel comfortable dating others and finding happiness in your life while helping this ex with his sadness? Would you be able to give real energy to someone new?

This isn't to say that you should forget about him altogether. You can talk to him about if/when its appropriate to check in. You can also ask him who else is around for him right now. It's great that he's seeing a therapist – having a mental health professional he likes is a very good thing – but does he also have any close friends or family members? If you know one of them, you can also check in about your concerns.

I'm sorry this is such a complicated breakup. Just know that it's not on you to be the one person who makes it all better.

– Meredith

Readers? How involved should the LW be in this person's life?