Dating New Guy after long period of singleness…Help!

Hi Everyone!

I read these forums pretty regularly but this is my first post. Basically, I am a 28 year old female who has had 2 serious long term relationships in the past (1 in high school and 1 in college for about 5 years). I have been single now for about 2 years and have recently tried online dating. I have had pretty bad luck but as of recent, have met this great guy who is 30, seems pretty stable, I feel really comfortable with, we have a great time together etc.

We have been on about 5 dates in the last month, all of them lasting at least 4 or more hours. Once we had plans to do a sunrise bike ride together and ended up spending the entire day together. We have been somewhat intimate but haven’t had sex yet and I like that he respects my decisions, never tries to pressure me. Also, 4 out of the 5 dates have been things he’s planned and actual dates.

The one downside is he is recently divorced (about a year and a half) and I can see it is still effecting him. He seems somewhat insecure about certain things or self conscious. He also has a pretty negative perspective about love, says things like he doesn’t really care about much regarding relationships right now, and that he doesn’t think he will find someone as good as his wife. I also think he is still on dating apps but I’m not that upset because it is still pretty new and we haven’t had an exclusive talk. He also doesn’t communicate that much in between dates but he also has mentioned several times has not super into his phone or texting like that. When we spent those 12 hours together, he looked at his phone maybe a total of 3 times. Also, I am the first girl he has “dated” (gone on multiple dates with) since his divorce.

So basically, I’m not sure if I should continue seeing him or not. Although I am someone who wants to be married one day and have a family, I don’t know if I necessarily want that this instant. There are things I still want to achieve in my life before meeting someone serious or settling down. But at the same time, I am not a casual kind of person (tried it a couple of times and it just wasn’t for me). I do tend to get attached to people and already feel myself liking him. Also, should I bring up the conversation about what he’s looking for even though he says other things implying its nothing serious. I just really enjoy my time with him and feel so comfortable, have been on other dates recently and haven’t connected in the same way, haven’t really met other guys in the 2 years I’ve been single that actually wanted to go on dates and not just hook up, etc. I guess I would be somewhat sad walking away at this point but also fear getting hurt in the future. Should I just stick around and try go with the flow with the possibility of things changing? I just don’t know if these things are 100% deal breakers or if he will become less jaded as time goes on and the more time we spend together.

Thank you all for reading and being understanding.