Okay, I was wondering if I ever gave a followup to this and I didn't.
So the same woman and I had some good conversations and then one day I mention I'm going to see some movie and she asks if she wants to see La La Land with her and her friend. I'm like sure, show up and then it ends up just being her and she said her friend wasn't feeling good. Now here I instantly thought about whether or not I should be like "riiiiight," but I didn't want to make it awkward so I just assumed she was being honest and went with it. We talked about it afterwards and it was a good conversation.
A week or two later I text her if she wants to have lunch, she's like sure. Conversation over lunch goes great, we talk for maybe two hours about all kinds of things and it's going super well. I'm not sure if she's into me or not but she makes some comments about how she always gets annoyed by dudes putting her in the friend-zone or treating her like one of the bros so I'm like maybe that's a sign she's interested. I mention something about doing this again sometime and she seems open about it.
So then I got super busy, ended up out of town. Thought about her every now and again but was kinda going through a bit of hell at work so I didn't text her until like two weeks later and asked if she wanted to hang out again when I got back in town. She said she didn't think of me romantically and thought we shouldn't hang out.
So next time I see her she comes right up to me and starts talking to me like nothing happened and I'm just there trying to be nice but also just thinking "what the heck?" This all happened back in late January and I think we've talked like once since then and I haven't seen her now for probably 3 months.
In retrospect, I think she was kinda just a flaky person. She showed up late to lots of things and then would say she would come to something and then just not come at all. Once I figured that out I swiftly moved on.
Disclaimer: I will fully own being an ass in this story and feel free to judge me as much as you want for how I behaved in this situation.
So most of the spring I'm generally resigned that my social circle doesn't have any women I'd want to date. That's cool until right at the end of spring one pops up that is a bit out of the mold for my social group and I thought was cute enough and was like, what the heck, why not? Except she was leaving for a good chunk of the summer.
And what's worse is I swear to god this was one woman I couldn't for the life of me have a conversation with. I ask her a question and she gives me like a two sentence response, ask a followup, another to sentence response. She would get excited, flirty and fun with other guys but the second I talked to her she was suddenly emotionless. That should have been red flag one but I'm pretty much determined to at least ask her out to dinner at this point because it seems like if I can get her to be more open with me it could be fun.
She mentioned that she would go on a date with basically any guy once. That should have been red flag two but somehow my brain interpreted that as a good thing. I mean, it's one thing to be open but she basically all but admitted she would go on dates with guys she wasn't interested in.
But it's all kinda moot because she's gone most of the summer and work is still kinda hellish and I gotta find a new place to move that's significantly cheaper because I'm quickly eating into my savings this year because the cost of living spiked up for me over the last year.
In the midst of all that, my AC breaks and I end up crashing at my parents house and I finally decide that I really just want to pull the trigger because I'm honestly at such a low point that getting rejected by a girl won't even make a difference at this point. That should have been red flag three. I was going into this with a devil-may-care attitude.
So I end up texting her and she's open and we set up a place and I show up and my goodness, it was bad. She shows up wearing the blandest dress I've ever seen her wear. It's like one of those plain pullover dresses that just looks like a giant t-shirt with a skirt. And it's this ugly shade of brown. Red flag four. She's not like the epitome of a classy dresser, but she looks pretty nice most of the times when I've seen her.
And oh my goodness this has to rank in the top 5 most awkward conversations I've ever had with a person. But I honestly just don't care at this point and proceed to just be honest with where I'm at in life and I probably sounded like a train wreck but my goodness anytime I tried to ask her anything about herself it was just two or three sentence responses. I'm throwing softball open ended questions and she's just giving the most terse, simple factual answers. It's like I'm almost talking to a completely different person than the fun-loving flirty girl that I've seen her be.
We talk for like an hour, well-mostly I talk and ask her questions she barely answers, and then I go to sign the check and there's this moment where I'm wondering what the CINECAST! I'm doing and why I even thought this was a good idea. The conversation lasts for maybe 10 minutes, she thanks me for dinner and we leave.
And my goodness it's a testament to my stupidity that I'm like, whatever, I'd still go on another date with her. I clearly wasn't thinking straight at this point and should have been aware of it and seen all these signs, but all I can think about is that flirty, fun girl and I think maybe if I just can sit down with her again I might be able to see that side of her.
Well, I text her and asked if she wanted to do something again. Unsurprisingly, she says "let's just be friends." And I'm like cool, but I think in the back of my mind I just wanted to hear her say it because I honestly don't think she was ever open to anything romantic and was deliberately standoffish. But even then, I also have no delusions that the date was bad and awkward enough that if she was interested, I wouldn't blame her for not being interested at this point.
And over the next couple of weeks, things start getting better for me everywhere else. New living arrangement rooming with a good friend and another guy I've met before, work stuff is still stressful but not as hellish, and other medical stuff gets sorted out some.
I look back and see red flag five: every time I saw this woman and found her interesting, she had a drink in her hand. Now I'm not saying she was drunk in any of these situations, but it became rather clear that a drink or two loosened her up a lot. Otherwise she's one of the most socially aloof and awkward people I've met and while I don't actively avoid her now, I do wonder what possessed me to even want to talk to her to begin with because oh man all the red flags are just waving in my face and making me realize that my judgement through the whole process has been abysmal.
So those are my two stories of failure to get any traction with two different women and how that was probably for the best.
As an epilogue, I will just say that in the last month I've noticed a couple of ladies I'm keeping an eye on although I'm aware that I should be a hell of a lot less devil-may-care with my attitude going forward. So maybe there will be more of these stories, although I hope less terrible.