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Romance, all signs pointed yes… But I hesitate…

Hey there.

So I'm in a bit of a pickle, and it's a weird one.

I haven't dated in years. For many reasons, one being I had a pretty bad breakup, where I was the other person in a cheating situation that just ended up bad. (No I did not know the other person, we were both played) Second reason being a few years ago I was diagnosed with a severe degenerative disorder that may or may not leave me somewhat disabled within the next ten years. I didn't want to force that on someone. Thirdly, I've been focusing on my career, and so far, I've made it leaps and bounds from where I was.

This last year I started/founded a non-profit organization/community. For just confidentiality reasons I will not disclose its nature. It grew quickly though; reaching about one hundred members, having multiple meetups, as well as donation drives for local charity organizations. A few months ago, a new member joined. A woman a few years younger than me. She seemed super eager to help our group and join the community. She'd been through a lot of hardships, both of her parents died, the last one dying a couple months after she joined the group. She also has a lot of severe mental illness', depression, ADHD, DID.

We held a meetup for our local PRIDE parade, and that's where I first actually met her. She was… enthusiastic to say the least, running and basically tackle-hugging myself and my friend who happens to be a member of the leadership committee for our organization. This woman was literally bouncing she was so excited to meet us. She made a few off comments that I was cute, but I paid it no mind. I played it off and kept things professional. I am supposed to be a leader and all professional after all.

A few weeks later, she started messaging the group leadership, idle chit chat. I responded but kept it professional. But the thing is, she kept flirting with me. Thing is, part of me wanted to flirt back. She is smart, into the same things I am, close to my age, beautiful, and very, very interested in me. As in she could have painted it on a billboard and still be less obvious than her flirtations. But I held back.

Her life. Whoo. I won't go into detail, but this lady cannot get a second of peace in this world it seems. Both parents died. She quit her job to take care of her dying mother. When mother died, brother quit his job due to an incident at work (completely not his fault, and something out of his control. Basically someone at his work got killed on the job because the place didn't care enough about safety, so a bunch of them quit in protest) now they are losing the house and she has a limited amount of time to not only find a job, but a place to live.

This last weekend was the first weekend since PRIDE that I'd seen her. (PRIDE was two months ago) We went to a local fair with a group of mutual friends from the group, as well as my best friend who tagged along. (He was totally casing her for me.) She was NOT quiet in her flirting. I drove her to the event, since she doesn't drive, and yeah, I think my face is perma-blushed. Definitely made her feelings known.

I asked my best friend what he thought, if she was too crazy or if it was bad crazy, he said, and I quote, "She's just the hyper kind of crazy. Dude, do it."

I had a tarot card reading at the fair, and it was scary as hell. I mean, I'm not one to be a strong believer in such things, but that reading had love all over. As in, even the reader was impressed. I hadn't even asked a question, she just drew cards, and everything seemed to lead toward a long term, maybe THE relationship for me. My friend is super into tarot and he said that two of cards I got were super like, holy shit this is a good one. Two of Cups and the Lovers. I was a bit spooked. The reader was so shocked by how specific the reading was she drew a second set just for the unnamed lover for the relationship, and same thing, amazing outcome.

To be fair, I now have a strong interest in tarot reading and want to start learning.

My concerns. She does not have a job. She doesn't have an apartment yet. She does not drive. There is a sort of aura of immaturity. Some of my friends are concerned she just wants to live with me, which is definitely a no go on my end. I'm on a lease, and besides, my place is too small for two people. This woman is a little less than two years younger than me, and while I either match our age or seem a bit older (I'm 28), she seems more like she's 22. I mean, I can't judge everyone by me, I had to grow up pretty fucking fast and I've got a lot, lot of just life experience that many people my age can't match. But at the same time, I can't afford to be taking care of someone. I mean, me doing the driving… she doesn't even have a DL.

Plus I have my leadership role. My group isn't super formal, and it's not running like a business, but how would it look if I started dating one of the members?

Just… Idk. But I can't get her out of my head. And… I don't know. I've never had someone this… into me. I'm not the type of person that goes out much. I work hard, take care of my own, and usually mind my own. If I've dated someone, it's always been a slow process and usually me pursuing them, not the other way around. I win them over. I've never had someone be that blatant and obvious toward me. Makes me feel like a giddy teenager, and part of me loves it the other part is a bit wigged out.

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