Well, hello, Dating-GAF. Been quite a while since I last posted in this thread. Just wanted to say that for all the great advice you guys gave me, I hated you guys at the same time, BUT only because you were right. So I had to stop posting in this thread. Constantly coming to this thread asking for advice made me worse.
So I've been doing a lot of better now thanks to taking a break from this thread. For those that are new in this thread, me getting back into the dating scene reaching close to my mid-30s made me a fucking mess after meeting women: The clingingness, not putting the phone down, etc, etc.. I turned 34 last Sunday, which sucks, and I always envisioned in my 20s where I would be in life in my 30s, but I didn't think it'd turn out like this.
Anyway, I do need some advice on this girl I've seen a couple times already. Things seem to be going good, but I may be overreacting on this.
Last Sunday night after I got off work, I texted her asking how her weekend was. She texts me saying how her and her roommates went to the beach. After a few playful texts, she said she liked me to invite me over that night. So I go over and hang out with her and her roommates. We have quite a bit to drink. I had quite a bit of bourbon. She even made me some frozen pasta. So nice of her to do that. Her roommates love me, 3am rolls around, and she says, "You can stay or go. Whatever your heart desires." I stay. She changes into some dress, but isn't a nite gown. She said I can get comfortable if I want. I'm wearing a polo shirt and linen pants, and all I do is just take off my shoes. Well, we're spooning, and holding each other close. I did have my hand down below, but she took my hand and put it around her chest. Sun rises, and I tell her how hot I am. I take off my shirt and pants. As I'm laying on my back, she rests her head on my chest. Her alarm phone goes off a few times, and as she checks her phone I did notice she wasn't wearing any underwear.
Anyway, we eventually have to get up as she has to get ready for work. We hold each other, kiss, and I leave.
Not going to lie. Me not initially taking my clothes off with at least just my boxers on, that's an exception, not the norm. Maybe it was the alcohol that made me do that.
So I texted her later saying I had a good time and her roommates were great. Also, if she was hoping for something more that night. She replied back saying it was nice just the way things happened with the blushing emoji.
Am I overreacting? Did it seem like she wanted to have sex with me? With her taking my hand away from her that I had down there, I'm thinking she may have been turned off by me not initially taking my clothes off, but then again when I finally did, she did rest her face my chest. I'd assume she wouldn't want to get too close to me if she was turned off.
We want to see each other again. Hopefully today again if theyre done moving into their new place.
Also, as we texted each other throughout this past week, she did say she's glad I think she's fun to be with, and she said she was a bit worried I would think she's weird. Her being worried tells me she's interested in me and doesn't want to spook or have me run away from her.
I'm leaning more towards overreacting.
Thanks, and good talking to you guys again.
From what you're saying, it sounds like there was certainly an opportunity for sex to happen if you had been a little bolder, but I don't get the sense that you've put yourself in a precarious position by
not going for it. Things should be fine, by all accounts.
Chances are, she probably misread the whole 'keep your clothes on' thing as a sign of unease or discomfort, but don't read that and kick yourself over it right away. You may have taken her out of the mood for sex, which explains her moving your hand, but here's the thing. I actually think you unknowingly did the right thing. I'll get into why in a second.
First off, you're a relationship kind of guy, from what I can tell. While you're far from horrified at the notion of having sex with someone you've dated a few times, your interests seem to be more focused on the long haul. There are plenty of guys out there that are only interested in stringing women along for long enough to get in their pants, but that doesn't appear to be the case with you at all. That said, the ideal girl for you is someone that recognizes and appreciates that -- whether a fluke of hesitation happened to you or not.
With that out of the way, here's why I think you may have done the right thing. In a roundabout kind of way, you established two important things with her that I'd dare say could lead to greater gains than if you had flung your clothes off and hooked up with her outright. The first thing you established is that whether sex is on the agenda or not, you still love spending time with her regardless. Secondly, you've shown that you're a human being that contemplates things, makes decisions, and moves based on your own inclinations and gut-feelings.
The first point is pretty self-explanatory, but I'm guessing the second one probably needs a little more detail.
At some point or another, we've all been guilty of overanalyzing things, getting in our own heads, or even chickening out in certain "gift-wrapped" situations as a result. And yes, it can definitely be a detriment to ourselves in many instances. However, that doesn't mean that we're always supposed to know the correct course of action, or the correct way of thinking. We're human, so we're still going to have plenty of those "should I, or should I not?" moments no matter how confident we are, how level-headed we are, or how comfortable we are with someone. Point being, it's okay to be unsure every now and again.
For guys, I have always believed that dating should never whittle down to a woman essentially telling them "here's a signal to do something... now connect the dots, meet my expectations, and don't fuck it up." Not if they're truly interested in you. A woman that's genuinely interested in you will be far more open-minded, patient, and just as interested when you don't do something as when you do. They'll accept the fact that you have a mind of your own, comfort levels of your own, hesitance of your own, and a rate of progress of your own enough to work
with you in the early goings.
So, the reason why I say that this was a good thing is because it seems like this girl didn't turn on you just because you didn't make a better attempt at hooking up with her. Now, that doesn't mean that you should continue to hesitate in the future. You shouldn't, and I think you know that because as you said, that's not the norm for you in those situations.
Shit happens, even when you're not a chicken-shit. Don't worry about it, keep seeing her, make light of it if she brings it up, and keep having fun.
That's my birthday, and Jhoan's too 
We should start a June 19th GAF birthday club. Happy belated birthday though (regardless of the date, if I got it wrong)!
Congrats on the intimacy, though. Keep going at that pace, like others have said. If you have enough dates where you have sex on the first or second, you start to overthink when it DOESN'T happen - like you're doing something wrong. The playa's dilemma, I call it.