How to not repeat asking out a guy who was just ‘being nice’ again?

I 33F broke up with a long-term BF 35M 6-7 months ago because he didn’t want to get marriage, won’t fix mental health issues and issues with alcohol. I’m dating again. I have a history of liking men who don’t feel the same way. I also struggle with not being overly reserved with guys initially. My ex had to ask me if I was even into him after date 5. On the autistic spectrum.

I moved to a new city with ex, and we broke up shortly after the move. So, I made new friends who knew I was knew in town and handling a breakup. I met a circle of people. One was a 37M guy. He talked about how he’s been single for many years, wah wah’d about not meeting ‘the one.’ I’ve heard and noticed a lot of women in town are messy, or just very picky, and it’s hard for men to date out here. So, I thought he just had a hard time meeting women. It seemed like we were flirting. He did lots of special favors for me. We had matching phone backgrounds. He walked me home and opened doors. Long text convos. So, I ask him if he’s interested. No. I later find out LOTS of women have showed him interest and he’s just very picky waiting for ‘the one.’

I’ve been on dating apps and I’m getting a good number of matches. I’m in an abundance mentality since I have several guys asking me on dates.

I’m in a ’30+ singles group’ that meets up once a week. I meet another guy 39M. He’s new in town (like me, kinda). He’s great. He hasn’t had a relationship in a long time and that might be because he used to live in a city with lots of men, few women and he’s not conventionally attractive. Or maybe he’s very picky like the other guy? There is another 42F woman in the group (group leader) I know he talks with outside of group but I can’t tell if that’s just friendship. We’ve been texting. I teased him about how I will use his love language more, positive affirmations and quality time. He asked mine, gift giving and quality time. He’s called me pretty, but he uses the term ‘pretty girls’ often. I think he assumed I wasn’t into him at first. I don’t show interest well. I asked him to help me install a water filter. First night, Home Depot was closed so he took me to dinner instead. Essentially asked me if I was over my ex and then didn’t want to hear another word about him. Second night, I cooked him food, we installed filter and talked all night. He picked up the parts I needed and didn’t take my offer to pay back. He even made a joke about how we are ‘married now’ and that make a ‘good team.’ But he also called me his friend when he picked up his dads call.

I dig him. I have other guys I’m messaging and going out on 1st, 2nd, or 3rd dates (in abundance mentality) with but he’s in the top spot. But I don’t even know if he likes me. I don’t know if he’s just ‘being nice’ like the last guy. I don’t know if I’m showing interest. I fist pump goodbye to other guys in the group but hug him bye … trying to give a hint. I’m doing good about not over thinking it. I don’t want to ask if he’s interest like the last guy! Can you give me advice on how to show interest and how to see if he’s actually interested so I don’t obsess?