Hello all! This is my first post here and I am grateful for the forum.
A bit of background:
I am 25 years old and I am getting ready to graduate from a university that will remain nameless. I've spent the last 5 years out of the dating scene. I've battled obesity, two bouts of clinical depression and a hell of a lot of self-doubt and crises of confidence. Even prior to the weight gain and the struggles with self-identity formation and depression, I developed a bit of a rep as a "nice guy." I had some successes in my earlier years but I haven't been physically intimate with a girl (no sex, no kissing, no hand-holding, nada) in 5 years. In spite of this glaring hole during what is often the most active and available pool of potentials any of us will run into, I have built myself into a self-confident, fairly charismatic, and interesting man. I'm secure with who I am and how I view the world. I've formed lasting, important friendships with people that enrich my life and I've taken up hobbies and activities that enhance my life. What lags so far behind is a semblance of sexual identity.
When I gained weight, I no longer felt attractive or desirable to women. Inside and outside, I felt lost. One of my closest male friends remarked that it's seemed like I am not interested in sex or being physically intimate with a woman in any way. It's true. If I couldn't find myself desirable, why would women find me desirable and why would they want me to engage them physically? I became the male friend that befriended women, some that I would date and others that I would not, and became the male friend giving the advice for how they should interact with males they were interested in, listening to their dating problems, and wondering what I was doing the entire time. I figuratively neutered myself and became the "nice guy" that always watches the girl he's interested in walk away with some other guy.
Needless to say, I'm over that. The problem is that some of the behavioral tendencies still remain. While I've hit the gym to work on my weight (I am still overweight by about 30 pounds), developed good and usable social skills, and realized that I have the ability to make people laugh genuinely hard, I still struggle very much with translating my interest into action.
Four or five months ago, I revealed to a girl that has been one of my best friends for almost a decade that I had feelings for her. After hearing about how nice of a guy I was and how the friendship was too important to risk, we agreed that we were best as friends. Nothing has changed, we are as close as we were before and I am grateful for this and other friendships. But I vowed that I would never let this sort of thing happen again.
Present day:
I have been spending some time with a girl as friends over the last few months. She's someone that I enjoy spending time with - the conversations flow easily, there are shared interests, she's intelligent...you get the drift. She's good people. I'm interested in seeing if there is potentially something more there but I feel like I lack the know-how in how to approach the situation. I've become quite adept at reading a room and reading the body language cues between other people but I can't seem to trust my instincts when these cues affect me. Because of my educational background and interest in human behavior, I've become an excellent source of advice, especially for my female friends seeking a male perspective. I'm credited with advice leading to 3 current serious relationships at the moment. All of this adds to my frustration because I struggle to inform myself in these situations.
My pace with this girl in question has been admittedly deliberate. I met her through a male friend of mine and we hit it off pretty well. In an effort to gauge her reaction, I forced myself to feel comfortable touching her when I am talking to her. I make it a point to casually touch her arm or her thigh lightly when I am emphasizing a point in conversation or trying to get her attention. She doesn't shy away but I don't really notice any "positive" reaction.
I guess I am to a point where I am uncertain of the direction I should go with this girl or any other girls that I am interested in in the future. My gut instinct tells me to be direct but I am concerned that perhaps I am not sufficiently building enough of a foundation and that I could be jumping the gun.
This weekend, I went out for dinner and a night of drinking with the girl I am interested in and three of her close female friends (at her invitation). Today, I was informed that the friends thought I was a good dinner and drinking companion and that they were "very glad" that I was there. I spent most of the evening in very good, fun conversation with all four. My thought is that if my friend isn't interested, there is a real possibility with at least one of her friends with whom I hit it off.
This has been a meandering post but what I am asking is this: How can I leave behind what remains of the "nice guy" tendencies that seem hard to leave behind sometimes? I am in a place where I am done with the bullsh*t games that "nice guys" engage in, the bending over backwards to be liked at all costs, the complete lack of self-respect, and the complete absence of physical intimacy. I am a confident, yet personally inexperienced, man. The inexperience is causing a small loss of confidence within my current situation and I don't want to the advice of these douchey PUAs that litter the web.
What are the major pitfalls I should be aware of in order to avoid being the infamous "close male friend"? With regards to my current situation, I've introduced some small changes in physical contact (it doesn't sound like much but it is a HUGE step for me) and I am uncertain as to how to proceed. Can you offer any insight for this? Finally, if this is a situation where this friend is simply just a friend, how should I approach the possibility of getting to know/date one of her friends from last night? My current interest is someone that I would remain friends with if there was nothing further in the cards for now.
Any and all insights are appreciated. I look forward to being able to reach out and help other members of this forum. If there are any points of clarification needed, please let me know.