Need Advice On Escalating Things With This Girl

Cliffnotes:
- 29, never had a girlfriend, very little experience with girls
- Sister introduced me to this girl, we message quite a bit, have TONS in common, but she's hesitant to hang out initially
- Got together at bar, things got pretty hot and heavy, but left at a kiss
- Next week was a little more awkward, slowly stopped contacting her
- Reopened conversation, going good again
- She invited me to meet up with her at a bar
- Emergency ER visit cut the bar short, stay with her at ER for 4 hours
- Go to concert the next day, decent conversations, but struggled to escalate with her
- Going hiking with her Wednesday, I feel like it's now or never with escalating things with her so she knows my intentions


Okay, so some quick background so you know where I come from and why I'm struggling with this. I'm 29, never had a girlfriend, a few dates but nothing ever escalated from them because I was self-conscious about myself and couldn't make the move. I started PMOing when I was around 18-19, was my worst from around 22-28, and have started the process of quitting around this time last year. I've had good streaks, 180 without porn was my best, but still have an occasional issue with mo due to loneliness. Very insecure and low confidence until just recently my whole life. Now I feel my main confidence issues are in social situations and with girls.

About 2 months ago my sister introduced me to this girl. We started messaging through facebook and we hit it off, and have ALOT in common, but when I started asking her to do stuff she was hesitant and avoided it, but kept talking to me. Turns out she got out of a 12 year relationship, has a daughter and deals with anxiety, so knowing this I feel better about her turning me down. Anyways every thursday night a local bar has team trivia. I told her about it and she was going already. We chatted randomly throughout the night but after trivia we started drinking and dancing, and stuff began to get pretty close. I ended up kissing her a few times, but it was awkward, because yes I have never kissed a girl before. It felt unnatural to me but nice as well. She left with her friends and we continued messaging some more.

We met again the following thursday and it felt weird at times and I let anxiety hold me back from pursing more. My sister and her friends pressured me into pushing myself yet I couldn't do it this time because it felt unnatural to me. One of her old guy friends was there and they were talking a lot and it killed all my confidence. I decided to stop contacting her for about 2 weeks. I messaged her after 2 weeks and the good conversations started again.

Last thursday she messaged me asking me what I was doing. She was at the bar and wanted to hang out with me. We did for about an hour, until she got a phone call from her doctors office to head to the ER immediately. She had some tests ran earlier in the day and they were concerned. I went with her because I told her if it's anything serious I didn't want her to be alone. She told me multiple times that I didn't have to stay but I did. We didn't leave till after 3am. She messaged me afterwards thanking me as well as thanking me the next day again.

The next night there was a concert at a local bar and she agreed to go with me to it. I picked her up, which boosted my confidence. At the concert we talked a decent amount but there was a bunch of awkward silence as well. We got close and she was receptive to me leading her around the bar, but for some reason I just couldn't get the courage in me to get closer and escalate it with her. At the end of the night when I dropped her off I told her to give me a hug, but that's about it. I know if I don't man up I'm going to lose her.

This wednesday we are doing what's called the incline, which is a mile long set of stairs along a mountain side, a popular attraction in our state. She told me when we first started messaging she's wanted to do it for years. I bugged her a few times about going, but sunday I was more forward about asking her, so she agreed to do it finally. I think because of the environment it will be easier for me to escalate things (done the incline 3 times, I'm not normally a bar goer). It's seems silly but my plan is to kiss her when we get to the top. I know I need to assert myself more too with her and make my intentions known, because it's already feeling like I'm getting closer and closer to the friendzone. This last weekend gave me some confidence that I might still have something with her, but I know my chances are running out and I need to man the fuck up. What gives me confidence though is it feels like she's still giving me a chance instead of ignoring me or by not showing interest.

I know this is a lot to swallow, but it just KILLS me that I struggle with this when I like this girl so much and how it feels like she has opened up to me to be more assertive with her.

I also know that I am WAY overthinking this and just need to man up. I know what I need to do on paper, it's actually doing it in real life that I'm struggling with, so any advice is greatly appreciated.

 

Are you a virgin or just never had a gf?

 

Both. I was always shy growing up and my interactions with girls in school were awkward and never went anywhere. When the pmoing started I lost all motivation towards girls (because I was being "fulfilled" by doing that, mentally), and whenever I tried I stumbled over myself and nothing ever went anywhere, blaming the girl usually instead of my errors in how I approached the dates.

 

I'm not amazing when it comes to woman but I have had a few great relationships while they lasted. And from my experience, woman like honesty. My advice would be to tell her your situation. Tell her you like her (dont tell her you love her) but that you've never been in this situation. That you had issues, very anti social and shy growing up and that you never got around to getting close to a woman. Tell her you'd love to change that and that you'd like her to be the girl to do that with. It sounds like shes giving you signals and that she is interested. You telling her will probably answer a lot of questions she is wondering.

By her not knowing that you've never been threw all this, she might think your not into her or that you don't have the balls to make a move. Woman get confused when they send signals and they go un-answered.

Its totally normal for you to find this really hard, it was super hard for me to make a move on my first girlfriend when i was 18. I can't even imagine how that must be at your age. Take it slow, let her know if you want to take it slow, she will understand. If you want to end up in a relationship with her you have to be able to comunicate/trust each other.

 

Hey thanks for the advice man, I appreciate it. You're probably right about telling her that, but I want to take action and let that speak for me. She's obviously interested in me, so I need to let my intentions known sooner rather than later.

 

I've actually read that specific thread and even wrote down a lot of what's said to refer back to it. I definitely feel like I've read up or watched enough videos to know what to do, I still just get in my head way too much when in those situations.

You're absolutely right though, all I need to do is stop being a pussy and just fucking do it. Nothing would feel worse than letting her move on by not manning up and taking charge, especially since she's giving me a chance to take action.

Thanks man!

 

Damn, just looking at what I originally posted makes me shake my head how weak and insecure I sound. I'm determined to make tomorrow one of the best days of my life, no matter what happens, because I'm ready to finally man up and take charge of my life!

 

@AnotherWay, hey man I know that feeling, and I actually did "call it quits" for a period of time. I actually told myself I was cursed to be alone due to my limited failures with girls. In 2010 I had an extremely attractive girl, who everyone was lusting over, ask me out to a bar and because I was so self-conscious and never went out and socialized I rejected her. She looked devastated and I felt like shit afterwards, more or less because I couldn't gather the confidence to be with girls.

Until I started getting more into fitness in 2013 I didn't even bother talking to girls that way, because I convinced myself I wasn't good enough. After some mild success I gained some confidence, and now after doing everything I have and basically cutting out pmo in my life, I feel I'm ready to take that next step.

As to your questions, absolutely we could still be friends. For a month (other than the one night), we've basically been that, but lately she's really started to show more interest in me, hence my renewed interest in her. Could we continue being friends? That's a hard one, but probably yes, because we have so much in common and it would be easy for us to hang out (we both love concerts and we've talked about going to some). Would I be happy with that? Probably not, but that would be okay, because I can only grow and learn from this, plus it's always good to have friends. I do know that it's my job to assert myself if I want it to be anything further than that. I am starting to fall a bit for her lately though, which is probably why I'm making myself nervous over it.

 

Fuuuck, I can relate to this so much. I'm 28 and still a virgin, though I've had "girlfriends" nothing ever serious though. I was dating a girl recently and was having the same problems you are. I finally told her my situation and we had a talk and made out a couple times and blah blah. Long story short she said she'd take my virginity, but didn't want a relationship or to be exclusive. I want a relationship, so I declined. It's tough in our situation, everyone else was figuring this shit out in high school or college if they were late bloomers. I'd try being honest with her and make your intentions clear so you guys can be on the same page. Good luck.

 

Thanks @Iscarpia87, I know I'm not the only one in my situation, but it's nice to hear others come forward. I'll come clean to her about my situation soon, but I think she can sense I haven't been with a lot of girls. You're right though, I need to get on the same page with her. What gives me confidence with her is that she has really only had one boyfriend, granted she was with him for 12 years, but otherwise she has her own set of issues when it comes to dating.

Yesterday went really great, I didn't kiss her but I did everything else right and escalated to levels I was comfortable with. I won't go into specific details, but I touched her a lot, hugged multiple times and held her hand. She brought up a concert that she wants to go to tomorrow to me yesterday and we're going to that. Mind you it's 2 hours away from where we live. I'm going to make my intentions known then.

It's crazy, but I've read book after book and watched video after video, but the best way to learn these things are by doing them. I could sense myself getting more confident as the day went on, and truthfully, for me and my past experiences with girls, things are moving fast and I love it.

 

sounds like things are going good and the two of you are getting more comfortable hanging out with each other. Glad for ya

 

So, hats off to you for introducing touching into the interaction! That's one of the hardest things to do for me. I've dropped the "I like you" bomb on many girls because that's what everyone always tells you to do.

Personally, I think you should just go for the kiss when you're hanging out with her:

- See how's she's reacting to your touch
- Get to where you two are sitting next to each other, maybe you can sit on one of the steps at the top?
- Look all deep in her eyes and slowly move in
- As you're doing this, watch her face for a reaction and also her body language
- If you get close enough without her seeming repelled, look at her lips, then her eyes
- Don't get too thrown off, you're basically looking for if she's completely disgusted or freaked out
- If not, suck some face!

It sounds like you are a fairly sensitive person from what I have read in this thread. If you are anything like me, I have a tendency to get very attached to a woman before anything ever starts. I rationalize by saying, "but we have so much in common"! (Having similar taste in music, movies, or beliefs.) And that I "don't want to screw this up!" That's why people say stuff like "There are plenty of fish in the sea", it's a mindset. And frankly, it's true.

I may not have had a lot of "girlfriends", but I have clicked with a lot of girls. In a way that I knew we clicked and I didn't doubt it for a second in that moment. However, I began to doubt it the more I rationalized why we should be together and the more I built up when I should make the move. The more that I think about it, those girls that I clicked with, it wasn't because we were made for each other. It was because I wasn't dreading anything, I was at my most natural and unassuming state of mind.

Point being that, the more you build up making your move, the more she will sense that dread. Which is why guys that go ahead and make the move really quickly, and persist even when rejected at first, are usually the ones that get the girls. Sometimes the girl isn't, "quite warmed up enough" to be ready for a kiss sometimes and you may have to try again. Not in a rape-y, creepy way, where she's like, "No fucking way, I don't like you that way and I never will." More like she thinks she likes you, but she isn't really turned on enough by the interaction yet to be ready for anything sexy. It sounds like you don't have a problem with being touchy, which is a really good thing in "escalating things" as you so eloquently put it.

That's why you get guys saying, "Just stop being a pussy and make the move." They are well intending, though kind of rude in saying emasculating/patronizing things, but more or less right when they say this. Either they just don't get what you're going through because they've never had that anxiety and therefore can't properly empathize with you or they just don't have the words to properly explain how to get over your anxiety without coming across like a douche.

Think of it this way. When you go to get in the swimming pool... Is it better to think about what temperature the pool is, if the pool has been chemically treated in the right way, are you going to remember how to swim after such a long winter or maybe it's even been years since you went swimming? Could some kid have pissed or shat in the water? Is the piss going to get in your mouth or go up your nose? Should you have eaten so soon before? Are you going to get cramps and then maybe drown? Or shit, maybe it's just going to be cold as hell and uncomfortable?

After all this overthinking, you ease into the water and you can't help but turn all of this shit over and over in your mind. The waters feeling really cold and you're shivering over in the shallow end. Then, you hear someone say, "CANON BALL!" They jump in and they're like, "Oh my god, it was so cold as I hit the water, but it feels so good now!" You continue to shiver with arms folded while staring at them. Then they say, "Dude, just dive in. It will feel good, I promise!" And, of course, you go underwater, feel all better and start splashing around for hours. My apologies for having taken the analogy and beat the dead horse that it is with a bloody stick.

I think that I finally understand why people tell you to drop the "I like you" bomb, as I like to call it, on people. It's not because it works. That's the secret they don't tell you. It pretty much never works unless, you do it in conjunction with touching and kissing. Trust me, I've told many women that I liked them. No touching, no kissing... Nothing, but the words and my god awful dread and the words themselves. I hadn't done enough physically for them to justify any feelings on their end, the words had no meaning or action behind them other than, "I'm scared shit less that you don't like me back."

Just kiss her, no matter how awkward and inexperienced you are, then, if she has a smile on her face or gives you sexy eyes, tell her that you are inexperienced and that you are doing this because you really like her. It will make both of you feel more comfortable, natural endorphins, if it's right and you won't feel as weird or unnatural saying the words. Now, that might work!

The reason people tell you to just go ahead and say, "I like you" is because getting rejected isn't the worst feeling in the world. It's the fearing being rejected that's the worst feeling in the world. The knowing that you are capable of this thing that's so easy to other people that you dread and yet you freeze as if under some sort of spell.

Btw, if you're interested, there is this lady named "Hayley Quinn" that gives dating advice on Youtube. She doesn't do that shit where she goes on and on and on about "That one little secret that will make her want you then and there" then go on for thirty minutes saying nothing of real substance, just hooks to keep you watching and then tell you to drop a bajillion dollars on some shady binder full of madness and negging techniques. The videos have valuable information on how to escalate things and she even has some videos of guys she's coaching making cold approaches. All of them available on Youtube for no monies. Enough of my droning on.

It sounds like you are miles ahead of me as far as touching goes and you already kissed her! Did she look completely disgusted when you did it? If not, what are you waiting for? The water is warm! Jump in the pool, mang!

 

Again, thanks for the replies everyone. So she messaged me earlier cancelling tomorrow's plans. I told her about a concert I'm going to in 2 weeks previously and mentioned to her to let me know if she still wants to go. So at this point, it seems things are slowing down again. I'm not going to give up, but I'm not upset either, yesterday was one of the best days of my life and I learned so much about myself and the areas where I need to improve.

I definitely don't want to drop the I like you line until I know there's nothing between us because I've done that before and it's always left me feeling horrible afterwards. @Dante Alighieri so much of your advice hit home so hard, especially the overthinking part. Also, I know she's sensed my fear and dread of building up to kiss or escalate more with her, which makes me look more like a friend than boyfriend material. Gotta go after what I want, and if she doesn't reciprocate the interest I can't let it bother me.

It's crazy, this time last year I would be doing my forever alone bullshit of crying alone because I messed up again, but now I'm more motivated than ever to keep building off the successes I've had with this girl so I can continue to grow and get more comfortable in my skin.

 

Keep that mindset going. Life is all about maintaining, no matter what craziness goes down. It's like as human beings, we're all artists and our art form is honestly expressing ourselves. Whether that be through our sexuality, productivity or just bettering ourselves in general.

It's good that you have an active social life. That's super important in keeping yourself from over thinking anything and it also sends the message to people that you're attracted to that you can do with or without them. In that you're always going to have a fun and full life! In a lot of cases it will make them want to join in.

Yea, do what you have to do to keep yourself open. You aren't committed to this girl in any way other than your determination to escalate things with her. Allow yourself to enjoy other women's company as well. You can do that without being a player. Practice conversational flirting with attractive women you see, waitresses, women you meet at the concert. You might even find yourself liking someone else more and that's not a crime by any means. Trust me, she probably flirts with other guys too.

All I'm saying is to not let yourself be swept way if you're caught off guard. Trust me, other guys will swoop in there quick if she's as cute and nice as you say. It can happen in like a day and it sucks because it feels like you've put the good work in and you got royally screwed by some jerk who just happens to know how to turn her on in just the right way. It's happened to me many times. Some girls will even do that to spark fire under your ass, which is fucked, but it happens. Don't fret it, just take it in as a fact. In time, you will becoming that swooping guy, just keep that in your mind. "I'm the swooping guy!"

 

Fuckin' right on man, your advice is dead on! I've been messaging her about the concert and she's all sad about not coming with me. Definitely making sure next time she does.

The whole virgin thing doesn't bother me, I mostly mentioned it so you guys understand how little experience I have with girls. Now, saying that, I'm not one to hold onto it until marriage, I just haven't been in the position, with my prior anxiety. Now that I'm feeling amazing and confident I wouldn't say it's a priority to lose it, but it's on my to do list!