To feel uncomfortable with this man?

It maybe that late night he got time to himself after looking after sister, forgot time and just assumed everyone has their phone on do not disturb setting at night. He sounds lonely which could make him a little over keen with having contact with someone. I would set out your boundaries though and say if you rather not use for chatting and only as contact about walks if late/not going etc.

Was his sister able to chat when you saw her as it maybe that he was trying to also give her some social contact. I can imagine if at home it's quite easy to fall into offering coffee while there and then dog walk. Men don't have the same worries about risks that women do so I doubt he even thought it maybe weird.

If you know a few dog walking people perhaps try to meet up with others in future and he can gain other friends. I think his reaction to this will also be telling. I do agree that sadly just being friendly to some men can be misread as potential interested even when there is no flirting and partnered.

Why would you give a random your number?

The only thing I would not be happy about is the 1am texting and would have to say something regarding this, but as a carer for my late mum most people don't understand how very isolating it can be your social skills take a nose drive and you struggle to open up to people, just making friends with another person seems difficult these days.

If your uncomfortable with how he is coming across just because he is a man then be honesty and tell him, he maybe shocked by how you have reacted as he seems like he just wants a friend he can talk to which you offered....but now your withdrawing that offer without being honest with
Him

Over tens of thousands of years, women have perfectioned an instinct that warns them when a male could be dangerous, or bring trouble.

Please listen to it.

Hmmmm... hard to tell with this one. I certainly wouldn't go back into his house though. For any reason. Even with the dog. Yes he's being friendly and he's undoubtedly lonely, but the night texts are overstepping. Sad to say but too many women have had experience of just being friendly taken as much more. And this guy is a prime candidate for this. His circumstances are sad, but they're not your problem. Definitely pull back. You're uncomfortable.... that's enough. I hope you don't dog walk in anywhere secluded either. What does your hubby think of it all ? Does he think it's iffy ??

I hate it when you've made plans with someone and they make you do something else at the last minute. It's controlling.
You can't fix broken, lonely people, even if you wanted to. I've tried and it's always gone badly. Why hasn't he found his own support groups or hobbies or meet up group etc?? It's all there waiting for him if can be bothered to look. The texting is a massive red flag. He fancies you. Avoid as much as you can.

As he is a carer for his sick sister he likely doesn't follow the same regular 24hour routine of most of us so 1am/7am texting is thoughtless, but not partucularly creepy.
You seem quite trigger happy sharing your number with people you say are just acquaintances so maybe stop this.
His loneliness has meant this friendship means a lot to him. Keep it going but ease off. Dog walk amongst other people if poss and less as one to one. Take hubby along as much as possible.

This is exactly why I avoid engaging strangers 😂. It was really kind of you to befriend him but personally I think if you don’t reverse pretty quickly you are going to be stuck with him

This ^
Trust your instincts they are there to protect you.

This nails it. They judge women by their own standards.

Not sure why I'm getting most of the blame.

Because putting the boot in and finding blame with the OP whenever possible is the specialty of AIBU posters.

Very good point.

He is a very private person but is able to open up to you. Ew. And offering to cook for you. I'd run a mile. He's taking advantage of your kindness.

I'm sure being a carer is very isolating.

But isn't it funny how so many lonely men seem to want to form friendships with women rather than men? I mean he could have arranged to meet with the ops dh instead couldn't he?

He's probably lonely and socially awkward. Being a carer is very isolating, it's a bit like living in a parallel universe where the real world carries on without you and you are on the periphery looking in.

So many men only bother conversing with women they find attractive. They therefore assume any woman who even passes the time of day with them must be interested in them romantically.... basically they judge women by their own standards. I used to experience this when I was younger at work...you'd say good morning and have a brief chat with a guy in the office and next thing you knew he'd be asking you out

@PuzzleMix My sister is OK now thanks, although she has never quite got over it and finds it hard to trust people. She is now very reserved, whereas I'll talk to anyone and she looks at me like I'm crazy if I talk to strangers in shops etc She is my older sister (10 years), yet I am very protective towards her and it's almost as if the roles are reversed and I'm the older one. That is absolutely awful about the man touching you after you offered him the paper. I hope you are OK, these things tend to affect you forever. Why do these men assume a simple act of kindness from a woman is a "come on"? I know it's not all men, but it's a sad world where you even have to think twice about smiling at a man, in case he takes it the wrong way!

NEVER question your gut when it's about a man. YANBU. You don't have to question the reasonability of a man making you unconfortable: no need for that. ALWAYS follow your gut. If you need to ask questions, do it after, never in lieu of following your gut.

It's sad, that as women we have to be so careful that something as innocent (and kind) as offering a friendly, listening ear to a man who has disclosed his mental health struggles and loneliness, can be misinterpreted and lead to a situation where you now feel so uncomfortable on your dog walks. You have done nothing "wrong" and have nothing to feel guilty about, you didn't lead him on in any way. It's him that has got this situation totally wrong and is now testing your boundaries. I really hope he gets the message soon and you can enjoy your walks again, it's so damned annoying that you tried to do a nice thing and now your life has been made difficult.

Some men are pigs

and yep no grown man should text a woman at 1am who he is not in a relationship with. Absolutely nothing to do with the OP 'showing signs of friendliness'. Just inappropriate and boundary crossing.

To the poster above I'm so sorry your sister was attacked - obvoiusly that had nothing to do with her being friendly - he was just a vile abusive piece of shit. He could have attacked someone who was unfriendly too.

YOu need to read the book the Gift of Fear

People here minimise your instincts - it's absolutely vital that anything that happened that 'rang slightly odd' with you you listen to.