Advice for first date with highly introverted girl

anon123

Space Monkey
space monkey
Joined
Jul 13, 2023
Messages
20
Hello all,

I have been bad at updating on a couple situations with girls I had asked about here before. I'll save the updates here, but just want to say thanks again for the excellent advice. Things went really well and I managed to shake my oneitis I was suffering from with the last girl in particular. Still talking, still sleeping together much less frequently, but didn't progress to anything serious. Been sleeping with other girls as well.

Writing now to ask for advice on a new girl I met, preparing for our 'first date'. She moved to town just six weeks ago ago and I met her on a night out with a bunch of friends. She has a few friends here already (that she moved here for, that I don't know). Through them she met a few female and male friends of mine, but last Friday was the first time she and I met.

First encounter: Long story short, we had a fun night night out in a group setting, she and I talked on and off (I was more interested talking to my friends as usual), but at around 10pm I offered her my spare bedroom (we were just a few blocks from my house) rather than take a 30 minute taxi home. On the couch at home we had a great chat, I escalated physically, she rejected saying that she never kisses on the first date and I joked that we hadn't even had a date yet. Made plans to meet again soon, then went to bed where we ended up making out all night with a lot of foreplay and oral but no sex. I know many will say I screwed up by not going straight for penetrative sex and ensuring she had multiple orgasms, but this is a girl I would like to see again so am fine letting her feel she is taking the lead (for now). Hell, she already broke several of her 'ground rules' for how dating starts, and I will keep gently breaking them but also want her to be comfortable (more on this and her past trauma below).

Next morning, took her out for breakfast after us having had zero sleep. The plan was to drive her home after, but she came back to mine for more making out, more foreplay, a short nap, then I took her to her place. The vibe was in general great all night obviously. Morning was still fun, a lot of banter, flirtation and teasing, but she also seemed a little stand offish at times. Could have just been lack of sleep and being exhausted, or maybe second-guessing her decision to move faster than what she says she normally does. Naturally, I am worried I did or said something to kill the great vibe we were having, but it's not like I really had much energy to sustain being at my best...

I waited until the next day and sent her a text to be polite and say I had a good time, and we've exchanged 2-3 texts per day since with a bit of chit chat until I finally pushed to make a concrete plan to meet up, two days from now. She has plans to crash with a girlfriend that lives a few blocks away from me that night as she has some work to do in this area the next morning, so she said she can meet in the afternoon or early evening.

My profile:
- 35 years old, ISFJ, soft/experienced
- Financially secure with a few small businesses here and online that I run.
- I drink a fair bit most weekends, sometimes every second or third when I am busy with work. Otherwise exercise 3-4 times per week and am in good shape

Her profile:
- 31 years old, probably ISFP but not sure, I think probably soft (could be wrong), I think experienced (again could be wrong), but definitely less experienced than me
- She is broke from the recent move but is almost done with her PhD and already has some freelance work that she is getting started with.
- She doesn't drink much and is obsessed with fitness
- One key thing she mentioned that she did not want to get into in detail yet on is some past sexual trauma. She mentioned how if we continue seeing each other this will be something we need to talk about just so I am aware of her triggers to avoid. Despite being very sexual with each other, nothing I did upset her so that is a good sign so far, but it's obviously something I will want to be careful and considerate about. She did cite this as a reason for ceasing escalation numerous times, just saying she would want to wait until the next time or maybe third time we meet to do 'certain things', and that she has learned with guys that the best thing is just that she needs to move very slowly with physicality until she feels safe.

On the situation: Both of us are a bit hesitant given that we have friends in common. She clearly was into what was happening and numerous times expressed she wants to meet again. She is ready for a relationship in general, but also said "this may go nowhere, and if it goes nowhere I'd still hope to become good friends with you" so wants to take it slow. I think she has also slept with (or at least explored had some physicality with) one or two guys in town since she arrived here by the sound of things. Honestly whether she has or hasn't is not relevant to me.

I was thinking that hooking up with me must be a bit scary for her given how she is new in town. I do not just know some of the same guys as her, but am also close friends with a few of the girls she is hanging out with and seems to want to become closer friends with (she specifically mentioned that the fact that I am friends with those girls made her feel way more comfortable and confident about proceeding with me). For my part, I am not going to lose my friends over what I do with her as they are good friends. But they are new to her and I imagine she is going to be worried about shitting where she eats as she wants to keep these new friends she has made.

I wouldn't be posting here if I wasn't extremely attracted to her, but trying to prepare myself mentally to not come across as too excited or wanting it too much when we go on that first date. I honestly think I erred a few times in this respect during our first encounter, flat-out complimenting her quite a lot and telling her I am into her. Am sure there are other things I screwed up on as well that I have not even thought of, but that's water under the bridge. I just need to make our next encounter incredible for her is what I am thinking.

My questions: For a relatively shy, younger, less experienced person than myself, but mainly given that she is new in town and has more 'at risk' so to speak by us escalating and moving toward potentially into dating (or becoming friends with benefits, which may be a good first step), what is the best way to proceed? On the one hand, I think taking the highly confident 'move fast' route and just getting her straight to my place for sex may work. On the other hand, given her vibe (and past trauma) I think she would be way more comfortable if I took her out for a fun activity where we have a chance to deep dive (this definitely worked with her, she is a more intellectual type and likes talking about emotions and deeper topics).

I just don't think the standard casual "let's go get a drink" will be enough for this one, given that we have already done quite a lot and connected pretty deeply pretty quickly in that first chat. Something a bit more meaningful (or just casual but also fun, as in some kind of activity together) would be better. There are also activities in my house I could propose if I just want to get her straight here, but I for some reason am thinking that won't be as well received by her for some reason. Maybe I will just casually lay out three 'options' of cool things we could do and see how she responds when we meet. My text game is terrible, I am much better face to face.

Sorry for such a long post. You guys have been hugely helpful to me in the past though and I want to get this one right as the first encounter definitely made a pretty incredible impression on me. Thanks for any advice!
 
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