I (35F) have been officially dating my boyfriend (38M) for about a month, but beforehand we were friends for a year and went on scattered dates since January. A lot of the "dates" were really just a one-on-one drink and then meeting up with our friend group for context.
Overall, I do really like him and enjoy spending time with him, but I’m starting to feel uneasy about the dynamic and I’m trying to figure out if it’s just early-stage anxiety or a real mismatch.
The good:
- We have a lot of fun together when we hang out
- He’s affectionate and we have a solid friendship base
- He’s funny, outgoing, and has introduced me to new places/music/social scenes
- He seems open to hearing me out and has shown some empathy when I’ve brought things up about boundaries with female friends
The concerns:
- Plans are vague or last-minute (ex: suggests a dinner date but doesn’t follow up with specifics)
- Communication is inconsistent, sometimes I don’t hear from him much during the day
- He goes out a lot late at night (bars, friends, etc.), which doesn’t align well with my schedule
- I don’t always feel prioritized , it can feel like I’m fitting into his life rather than us building something together
- Some boundary stuff with female friends that has made me a bit uncomfortable. He's very close with a female friend who he used to hook up with and have feelings about. Others even noticed the dynamic and encouraged me to flag it. I did and he was understanding. However, he'll post suggestive instagram stories with other female friends and comment heart eyes on their pictures
- Overall it just doesn’t feel very structured or “relationship-y,” even though we’re official
For context, I was previously in a long-term relationship/marriage that became really unhealthy toward the end, and I think it made me value consistency, clarity, and emotional security a lot more now. His personality was a lot different, too. He was introverted and avoided going out, while my current boyfriend is very charismatic and outgoing, so I'm trying to navigate dating that kind of personality.
I’m trying to figure out:
- Is this just normal early-stage, more laid-back dating that I should relax into?
- Or is this actually a sign of a lifestyle/expectation mismatch that will keep bothering me?
- At what point do you expect things like planning, consistency, and structure to show up?
- Am I being too rigid, or are these pretty baseline expectations?
I would be sad if things didn’t work out because I do like him, but I also don’t want to end up in something that makes me feel anxious or uncertain long-term.
Would really appreciate outside perspectives. Thanks so much!