Asking for a 2nd Date or not - What should I do?

Hey everyone, a quick question: I’ve been out of the dating loop for a long time so I’m not really very good at knowing what I should be doing. I’m a 30 year old woman and I’ve just got back into dating after being a long time carer for my father. He passed this past December and I’m now getting out into the world and trying to build a life. Part of this entails dating. A friend of mine suggested that I should join some dating apps so I duly downloaded Bumble and Tinder. I haven’t really met anyone through either app yet apart from one guy who is actually a mutual friend of a an old school friend. He went to my high school and we grew up in the same town, went away and now both find ourselves back in said town. I knew his name but didn’t realise any of this or that he was this guy until we began talking via Whatsapp. We seem to have a fair amount in common and he seems a nice guy with a good personality, though not someone I’d pick physically, he's 35 and a self confessed nerd. We went out for the first time last Sunday after four days of really great chatting via text. We met at a local river and walked our dogs, we’re both animal people and had a great time walking. He also tells me that he’s been hurt before and been in two long term relationships. So, I’m aware that I might have to go slow with him but I’m fine with that. I don’t know if he’s shy or just not interested. He text that night but has been quieter since. I spoke to him briefly on Thursday night but he seemed distracted. I’ve left things for a few days because I don’t want to be blowing up his phone every ten minutes. Now, I was thinking that it would be cool to meet up again, either for a coffee/drinks or for another walk with the dogs as I feel like he’s an interesting guy. I don’t want to come over as desperate or overly interested at this point but also just feel like if he’s interested then he’s interested or not regardless of what I choose to do. I know I’m overthinking WAY too much. He's been burned, I'm lacking in experience, I feel like we're the blind leading the blind here. Would you suggest I leave it and let him ask me out (or not) or if I should go ahead and ask if he wants to grab a drink/go for walks myself? Thank you for any help you could give.

You're overthinking it, at least at this point. He might just be assuming that you're rejecting him so he's not trying. On the other hand, he might be too damaged to date. Guys like him usually take a little bit of digging to find the real him.

He likes dogs, so that's always a good sign. I've met tough-looking biker dudes who you would run away from walking their dogs and they become absolute sweeties when you start petting their dogs and asking their names.

Anyways, he's the type of guy you might have to pull out of his shell. But definitely ask him if he wants to walk your dogs together and go for coffee. Just talk with him. Nothing heavy. Look for warning signs but also look for things you like in a guy. Treat him like you would a friend and just be yourself. And see what happens. You're also free to date other guys too so don't feel that this guy is your only chance at dating. But see what happens, and don't be afraid to ask a guy out.

Sorry to hear this. He sounds interested. Scale back on text convos and ask him out. But focus on in person meets and do not over saturate with texts like this or place this much emphasis on texting.

We met at a local river and walked our dogs, we’re both animal people and had a great time walking. I was thinking that it would be cool to meet up again, either for a coffee/drinks or for another walk with the dogs as I feel like he’s an interesting guy.