How to proceed with this woman I'm talking to without overdoing it

[Herkamer]

This one's a long one, so please bear with me.

So there's this woman, named Hope, that I had been friends with for over a year and only in the past 3 months I've been noticing things that have me (cautiously) optimistic. I met Hope, and her sister Heather (who's married), back in May 2021. I didn't know what to think of these two, other than they were both good looking women. I also thought, at the time, that "well, there they're going to be mean to me because I haven't met many good looking people that were actually nice to me." I wouldn't say I'm bad looking but part of my problem is I use to be very overweight and had image problems during my 20s and early 30s. Now, I've lost well over 100 pounds, working out everyday, dieting properly, more active physically, changed out my wardrobe, and I've been doing ballroom dancing for nearly a year and a half. That's how I met Hope and her sister, at a ballroom studio. I noticed, overtime, that they weren't stuck up or arrogant or ANY of the stereotypes that I encountered. Actually, they're really cool people. At the time, though, I thought Hope was with this one man during the Summer of last year. Turned out they weren't and it was the guy simply chasing after Hope. One of those nights, when I thought they were together, I got to know more about Hope. The things I heard from her, man, I NEVER would have thought she had the interests I have. She's into sci-fi, board games, Halloween stuff, cello quartets, I mean this was stuff that's right up my alley and I LOVE to do and check out. She blew me away and I felt so bad for judging a book by it's cover. Still, I didn't hold the interest I do now because I thought I didn't have a chance. By the end of Summer 2021, Hope and her sister, Heather, weren't able to come back to the ballroom studio due to work, but they had invited me to stop by the coffee shop they both worked at (which Heather and her husband owned, at the time) whenever I was in town. I did, eventually, probably 2-3 months after they left and only went there when I was running an errand up there.

Fast forward to February 2022. At the time, there was another woman that had (and I suspect still does have) interest in me and we were going to meet up one day along with a friend and another person. I go to the coffee shop where Hope and Heather worked at to grab something before I go meet up with this woman and small group. Hope and her brother-in-law were both working that day, and I found out that she had a date later that night. She doesn't go out much with another guy, and she does it only to get her out of her home for awhile. She's got a kid, and the father of the child was, I believe, the last real relationship she had been in (and I'm guessing it's been a few years ago). On top of that, she doesn't let on to her parents that she's going out. Probably because she doesn't want to make a big deal out of it. One other time I was there, I asked how her date went and she tried to keep it on the down low because her dad was there. I felt bad because she didn't want her dad to know she went out with someone. Turned out, though, the date was a bust and she hasn't spoken to this guy since because I apologized to her later on FB messenger. But she said it was all good and no need to worry. Since then, I had found out she hasn't been in a relationship since the father of her child were together. And after that encounter, I had another with this woman.

At the old studio I was at, we had a Latin dance party on a Friday night. To me, it was another party that this studio put on, which were always fun. Out of the blue, literally one week after our last encounter, Hope came back into the studio that night. She was invited to come out, and I got to not only talk to her but also dance quite a bit. My younger brother, who has autism, even got to dance with her. Since they first met, Hope and her sister, Heather, have been so good to my brother. They've been patient with him and always enjoyed dancing with him. They don't treat him like a little kid or anything (he's 29 y/o), so that tells me something about them. Anyway, Hope told me she was going to try and make it out more and that she had been so busy. The nights she has off she usually ends up being with one friend of hers and her sister. She had told me about she likes to have a movie night night and watch a franchise, like she had a hoodie on from one of my all time favorite sci-fi series and found out she had watched all those movies in one day with a group of her friends and sister. So that was something else I had learned. A few days later, at the studio, my cousin, who was coming with us at the time, and myself got done with our private lessons. Hope, once again, comes in for a lesson of her own. My cousin met Hope last year as well and thinks she's a good person. They had talked quite a bit last year and likes how she use to complement on his wardrobe from time to time. That day, according to my cousin, Hope had only paid attention to me. He said we were talking and were a little playful with each other. He told me he wasn't upset at all because he had told me don't write her off, and that she might have been showing interest. I took what he said under advisement and time moved on.

Eventually, this past Summer came and I started noticing more. I had contacted Hope originally because I was planning on changing dance studios, and a friend of mine thought Hope was taking lessons at this one place I was looking at. I reached out to Hope and asked about them, but found out she wasn't going. The subject changed and we got to know about each other a little more. I found out that she, too, was overweight when she was younger. Looking at her, this woman, in my eyes, is beautiful, and it struck me that she was once like I was. At the studio and at a get together with the other students, guys ALWAYS chase after her. She leads none of them on, either. They're in love with the way this woman looks. But, from what she had implied, none of them really took the extra time to get to know who she was. If they did, they must have found out that she wasn't who THEY thought she was. So we have something that we had in common and can relate to. Anyway, we planned out a night of karaoke with the other students and started inviting them. Her sister didn't show up, but the others did. One of the first things she did when she walked in was started talking to me, and we had spoke for about 10-15 min straight. We did a song together, and, wow, talk affection she was showing off. We danced together, shared drinks, and she even wanted me to go somewhere else that night with the group. After that get together, we planned out another outing, this time, involving a jazz club. Same deal as before, except I FINALLY got her phone number, and when I asked she put HER PHONE in my hand so I can text my phone. So that definitely to the point, for sure. Since then, I had been in contact through normal texting instead of relying on FB messenger.

The month of August came and I had got word from members of the group that Hope had got a bf. So almost for a whole month, I had no contact with her. But before that happened, I had talked to her and her sister, Heather, about a get together that involved a winery. We didn't know everyone's schedule and we wanted to go. So I got a hold of Heather and asked if she, Hope, and Heather's husband would want to go. And I had mentioned if Hope wanted to bring anyone she could. At the time, even though Hope, I thought, had a bf, she's still my friend, and I didn't want to short change her on that. Well, the night came and it was only Heather and her husband because Hope was sick the night before, which was fine because we had a good evening. During that time, I was bold enough to say that I heard that Hope had a bf. Heather looked at me strange and said "NO, she doesn't." Then she goes on and explains what Hope had told me before. Actually, the person Hope WAS going to bring was her FATHER. Before, during the Summer, Hope had, more or less, invited me to a Father's Day get together at a brewery with her family. It got cancelled because schedules weren't agreeing and hardly anyone could make it. After the winery night, I shot Hope a message, letting her know that we missed her the night before and I hope she gets better soon. She responds almost immediately and we've been in touch since (which was Labor Day weekend).

Now, a week ago, Hope invited me to a bar crawl this coming weekend (October 2nd). Two weeks from this weekend, she wants to go to a haunted house because she loves doing that stuff (as do I). And we're even talking about going to see Trans Siberian Orchestra with some friends. Already, she wants me to go do stuff with her. Which brings me back to being cautiously optimistic. I don't want to screw this up nor get overly excited. This woman, every time she messages me, the texts are, basically, 2-3 small paragraphs long (sometimes longer). Thing is, number 1, I NEVER dealt with a woman like this before (especially with how beautiful she looks), and number 2, I've been burned before in the past by other women and it doesn't feel good at all. I mean I went out with someone over a month ago but nothing came from it, and earlier in the year, I did with another woman (But, again, nothing happened). This one has been very consistent with me and we have fun every time we get together. We enjoy talking to each other face to face A LOT, and she wants to catch up from this past month. I apologize for the long post, but I just wanted to put as much context out there as what I can. And as the title of this post goes, how should I proceed? I'm going to the bar crawl and I do want to do the other things, but what would I do in case if things start happening between us? I had thought about asking her out to my office's Christmas party, which would be a dinner and show on a train. Even then, I don't know how soon is too soo and how late is too late. Suggestions would be helpful, but PLEASE be gentle because I am nervous and really don't want to screw this up. Thanks for taking the time and reading!

[Wiseman2]

14 minutes ago, Herkamer said:

I'm going to the bar crawl and I do want to do the other things, but what would I do in case if things start happening between us? 

It's going great. You'll have to play it by ear. Leave past baggage in the past. That's all you can do.

[loved-and-so-lost]

I think the long post was helpful for understanding the relationship that has been forming. I think it sounds like you have an undeniable connection and I think that is a truly beautiful thing. You both sound like very fun active people I feel like you both complement each other well, and the fact that you have both been though some of the same things also makes it easier to relate to each other.  I think that you should definitely go for it. It is better to have taken the step and see where it goes than to have never have moved forward at all. I believe in you!

[Herkamer]

So to give an update (and forgive me for another long one, but I just want to add context and that there's no confusion):

The bar crawl went well! Hope actually explained the situation about the rumored bf. This may sound confusing, but bear with what I'm about to say. So there was a guy involved, but it was, more or less, she found interesting enough to give a chance to. He had taken her out a few times and the guy was pushing to get into a relationship with her. This turned her off pretty quickly when he had become pushy, and she had, eventually, stopped talking and seeing him altogether. As she put it, she was single but exclusive to him. in other words, she was seeing him but not as bf/gf (at least not yet, which didn't happen anyway). But she told me at the bar crawl, and from what it sounded like, she wasn't really interested in him. It was, more or less, curiosity. Other than that, she sat with me most of the night and we planned out our haunted house trip (which I'll get into here in a bit). So that was a fun night.

 

The following week, on a Friday night, I was at a large ballroom for a b-day party for a friend, who's also friend's with Hope. Now, Hope rarely goes to this place, while I do go frequently because I'm in ballroom dancing. They had two rooms playing two separate kinds of music and different dance styles. I went into the smaller room with one of the female students and started dancing with her for awhile. My cousin and brother, who were with me, apparently, had been trying to get my attention, but I was so preoccupied dancing I didn't know they checked up on me. After I got done, my cousin said that my gf was there. I thought of someone else because she's always an attention hog, but my cousin said "no, your gf is here." I was so confused because there were a few other women I was thinking of I know that are not interested, and as I looked, I saw Hope, who's hardly EVER in there. I didn't want to impose myself because someone was talking to her while she was sitting down and another friend of mine came up to talk with me, so I did that. When she and I finally looked over at each other, I waved at her, like a greeting wave. After I did that, she walked right over to me (not me to her) and we started talking for about 15 minutes. She admitted that she's not very good at responding to text messages (but always good at checking emails because of work and school) because there would be times where she won't respond for a few days. After this one guy tried to interrupt our conversation nearly 3 times by asking her to dance, and her telling him it'll be a moment, she asked me if I wanted to dance instead, and we did for about 15 more minutes, while we still talked. We even had a moment where we were dancing and we just stared into each others eyes for almost a minute. We probably hung out for nearly an hour that night, and we walked out together when the place was closing up. So another good evening (and an unexpected one, too).

 

This past weekend was the haunted house. Hope, her sister, and her brother-in-law came with my brother and I. When we met up before we hit the road, we had finished off a thing of bourbon I got her after my trip to Kentucky this past Summer. As we were heading over, we talked about going to a martini bar and some food before. So she was looking and we decided on pizza. I went ahead and gave her my card so we can do it up quick. She went ahead and ordered, and by the time we were about to walk up to the martini bar, the pizza place we thought we ordered from, which was right across the street, was a few streets over. So everyone else grabbed a table, and Hope and I jumped back into my car to go get the stuff. It was our first one on one alone time with no one around for about 10 minutes or so. We got to know new things about each other, and even when we got back to the martini place, we sat in the car for a few minutes talking. Afterwards we went in, deciding what to get, then Hope went up and, not only got me one but two drinks, which I never asked her to buy either one. She just did it because she wanted to. We put those down quickly, went to the haunted house, and had a good time there. At the end of the night, I brought them back to their car, and, I swear, Hope gave me the longest hug I think I ever got from her. It was like she didn't want to let go. As my cousin put it, Hope seemed like she didn't want to leave, but we had to. Either way it was another successful night.

 

Now, I should feel ecstatic, and I am because she told me she's on board for Trans-Siberian Orchestra in December (she's never seen them live before), I'm still nervous because I haven't heard from her. But I need to remind myself that she's done this before and has kept her word and responded when she gets around to her messages, even if it has been a few days. I had asked her if she and her sister had anything planned for the next two weeks because on the way home from the haunted house, they had talked about doing something for the rest of this month but haven't pinned down as to what it is. I don't know, and maybe she doesn't want to move too fast, either. I know that she does like me, for sure, but how much is still yet to be seen. I just thought her buying me two drinks, hanging out with me for nearly an hour, looking into each other's eyes for nearly a minute with no words, and her wanting to go to TSO would be good indicators. Again, I never dealt with a woman like this before, and I'm trying to take my time and not rush nor be pushy. She was going to get back with me when she talked to her sister, brother-in-law, and a mutual friend of ours about going. The only thing I said to her was I may have people interested in going and I'm waiting to hear back to see if they ACTUALLY are going, and that I was wondering what her and her sister are doing the rest of this month because I'm trying to plan out mine. I was the last one to text and that has been since yesterday (Oct 17th) and she texted me the day before (Oct 16th). But up to this point, do you think things are still going in the right direction?