Do I chase this man?

[Daffodildelilah]

I’ve been casually seeing a man for five months who is going through a divorce and is struggling financially, losing his home etc. In person we have a great connection and fancy the pants off each other. I stupidly have allowed myself to fall for him. He is very open about what is going on in his life and is pretty broken currently by it all. He admits he feels depressed and has withdrawn from people as he feels worthless.

He has stopped keeping in touch as much and is seeing me far less than he used to. He won’t go out on dates because he has no money and doesn’t want me to pay. I’ve asked if he wanted to end things and he doesn’t. I don’t know how to handle this. I don’t want to walk away as I think a lot of him but I don’t know how he feels about me (he doesn’t seem to know how he feels about anything right now as his life has fallen apart due to money). I feel like I am the one who mainly gets in touch, ask to see him etc. I don’t know if to step away and see if he makes an effort but i’m worried he will think I don’t care if I do.

In short, no.
He's way too much hard work.
Move on.

The man he is without all these issues going on is someone I really care for and admire. But I can’t seem to find a way in.

Given your friend’s situation, he is in no place to start a new relationship and, to be honest, expecting him to is a bit unrealistic.

It sounds like what he needs at the moment and for the foreseeable future is just friends. People who have no expectations of him, and are happy simply to listen. If you’re happy to be just mates, then fine, but if you need anything else, I’d move on.

It seems to have inadvertently turned into a fwb situation. While I am ok with seeing how it goes while he gets his life together, I’m scared he will sort himself out and then commit to someone else.

He needs space to get back on track before starting a rations hip.

Tell him to contact you when he feels ready and respect him not contacting you in the meanwhile.

Would you keep in touch by messaging every few days or just leave him to it until he hopefully gets in touch out of choice ?

I'd just leave it. You sound more into him than he is to you. Wouldn't you rather be with someone that makes it clear how special you are and how much he likes you?
Half the time when men say they need to sort themselves out it's because they aren't that into you. If he really really wanted to make it work with you he would be making it clear and you wouldn't be feeling like this.

I don't think he's in the right place to start a new relationship, but I wouldn't step out if his life completely, can you support him as a friend for a while and lower your expectations of a relationship happening?

Having just lost a friend to suicide I feel it is very important to stay in someone's life when they are down and appear to be pushing you away, even if it is hard work.

I want to stay in his life for the time being. I had depression four years ago after losing my baby boy to stillbirth and the subsequent breakdown of my relationship. I didn’t want to see anyone, I withdrew and made excuses from every social situation and I barely was able to think straight enough to know my own name let alone treat someone else with respect. I know by how he is in person that it isn’t deliberate but it still doesn’t help in terms of moving anything forward.

No. Give him space.

By space, Flower777, do you mean not contact him at all?

No. Be kind to yourself, from your posts you’ve been through enough in the last few years.
Let him know you’ll be there as a friend but get out there dating others. Stay in touch but keep your distance until he’s in a better place as he’s not your responsibility.

I know dating others is the right thing to do but I have so many feelings for him, no one else measures up. I keep hoping he will sort himself out but i’m Aware that I can’t waste my life sitting around waiting.

No. You don't chase anyone. It's a waste of time. He's not in the right place to date right now. You need to accept this and move on. Just stop contacting him. And you don't have to put pressure on yourself to date others, you don't need to date at all.