Defining the relationship early a buzzkill?

[bgrasshaker]

Any suggestions for a guy not sure about having the talk? It is a little early, but I have a limited amount of time leftover to invest in a relationship and need to cut to the chase. I am back to single life after 14 years and what used to come intuitively now escapes me. There's also a good friendship at risk.

Started hanging out with my long-time stylist a couple months ago. She's 10 years younger and just off a very short/very intense relationship. I've had a ridiculously tumultuous 12 months and we hang out, party a little, have good convo always and commiserate some. She's a tiny bit of a mess, can't get out of her own way, aloof, but I like that she's very self aware and knows no denial or hypocrisy.

About a week and a half ago, we went to a concert and followed it up with a couple hour makeout session. I initially assumed that might not be an uncommon occurrence for her, being a straightforward 30+ y.o. and something of a party girl. The one thing that did stick out to me was how when we started making out, she pulled back and told me how (total paraphrase) she thought i was an awesome guy and an awesome dad during the aforementioned tumult. Nice, but not the "I've been wanting to do that/you're hot" that I remember typically coming at that moment. I almost sensed pity, for lack of a better term. Anyway, eventually stopped smooching and went home.
Couple days later, had to meet to swap something and ended up having dinner, with her skipping a date/guy that we both agreed sounded lame. Agreed we had fun, light kiss good night. Couple days after that, had to swing by and grab something before leaving town, usual convo session, light smooch good night.
Since then, she seems standoffish. We've never had extensive communication other than in person (which is a sporadic occurrence), but her texts are noticeably more brief than usual and I just get a weird vibe.
I'm in a place where I'd just as soon get to the bottom of it sooner rather than later. But, I don't want to ruin a good friendship or a shot at seeing if there's more by coming off as overly anxious or misinterpreting. Avoiding awkwardness (nevermind the potential rejection) would be ideal.

Any thoughts on timing or a potential phrasing? I am paralyzed and starting to over analyze.

[michelle23]

I think if you leave it much longer then your gonna mess up. Shes starting to friendzone you coz your not showing interest. Ask her out on a real date and let her know you like her. If you want to date exclusively then hurry up and let her know

[Mattiemae]

That was my thinking too, she may think you're not interested in her, and disconnecting because you were showing interest, but now she don't know what to think or do. Really you need to take it slow with her, because you stated she is messed up. Define what is messed up? Just having a hard time letting go, emotions all over the place? Unstable, with mental illness? lol Hard to know what you mean by messed up. If it is she is just having a hard time with life style changes since her break up that is all normal. She may feel alot better if she is with you and move on with her life.

Really you have to figure out what you want with this woman, but never rush or hurry because of your age, or time. Relationships take time to grow, and develop. You've showed her interest, so decide whether you want it to happen or not. Otherwise it will be to late if you don't acknowledge you want a relationship with her, because as a woman a guy either likes you as a friend, or girlfriend. So we revert to the friendship part if the guy doesn't show he wants more. lol it's kind of black and white thinking, but stops the confusion in the mind, and stops us from making emotional attachments.

[bgrasshaker]

Messed up = over the years of knowing her as my hair cutter, she's been very open about what goes on in her life and that seems to include a lot of partying, a pretty liberal approach to sex, a traumatic childhood and she just seems to be a little scattered in general. I know, she sounds toxic. But, what I've grown to like about her is that she's smart as a whip, very very self aware and not at all in denial about her issues. Very independent and open too. The little I've observed of her relationships hints at not the greatest guys.
I forgot to mention that since making out I have taken her soup when she was sick and gave her some good books as a gift. So, I'd be surprised if she thought I wasn't interested. Still, I haven't had any luck getting her to hang out lately and her text responses are very brief. Just makes me think she regrets getting affectionate.

[Mattiemae]

I know whe don't like to communicate with people out of fear, but really it's the best way to get to the bottom of things. It's just so much simpler than asking other people for advice. Really we need to push through our fears and know it's not as always bad as we think it is. Worst case scenario she doesn't want a romantic relationship. There's other woman out there. The thing is when we communicate and respect each other than it is easier to keep on being friends, even if we don't get what we want. The best case scenario she wants more than friendship. Well the thing is talking things out always gives you the positive results in any case scenario.