As pertains to this post, I'm not looking for commitment or intercourse. While those are things I'd like to find in some more serious or long term relationships, and that might develop from something simpler, today I'm concerned with other less involved kinds of relationships.
I don't think I can contain in a single phrase what I'm looking for. Perhaps "companionship" is closest, but that doesn't necessarily cover the full span of degrees of intimacy, or lack thereof, in question. There are a lot of relationship niches, and most of them are empty in my life most of the time. I'd like to find someone(s) that I can have lunch or dinner with. Someone to see a movie with, out or at home. Someone to take, or by whom to be taken, to parties of all sorts. A partner in exploration and mischief. A warm body to share cold nights with, even just for the comfort. An intimate partner, somewhere along the spectrum of first through third bases, inclusive. Everything in between, and combinations thereof.
I am constantly surrounded, admittedly by my own choice, by friends and acquaintances who have no problem filling many of these niches on a regular basis. I feel inadequate in being unable to emulate them, and distraught at failing in my attempts. I know that I have friends who envy the life that I live, and I've already made so many steps in the right direction from living a boring life, but I see so many more ahead of me and am unsure of how to take them. This is a difficult topic to bring up in casual conversation, as other people's relationship problems are rarely fun to talk about.
Admittedly, I am somewhat shallow. My "type" is less specific than most, but not nearly enough so to be described otherwise. I limit myself by being more selective than I must about who I interact with on different levels of intimacy, based purely on physical characteristics. I've learned a lot in the last few years that has helped me decrease the severity of this problem, but it's not going away any time soon. I'm including it here for the sake of completeness. I also have intellectual and philosophical criteria, but fortunately I prune my casual friend network sufficiently that those only come into play for people I plan to spend more than a few hours a day with.
Many of my problems are due to a fear of rejection. More rationally, due to a fear of the fallout from rejection, specifically rejection caused by negative reactions as opposed to just neutral or lack-of-positive feelings. I resolved this year to be more forward and direct with the girls that I want to be more involved with. So far I have had some success with this approach, but also a few failures that significantly damaged what little relationship I had previously with the people in question. This mostly boils down to a risk/reward problem. I feel like I am relatively good at the 'risk' half of the analysis, but the 'reward' is where I need to apply some tweaks. Specifically, I have to decide on the relative weights of various outcomes. How many relationship-damaging failures are worth enduring to find one good stronger/deeper relationship? What is the negative weight of the social stigma gained by otherwise non-damaging failures?
I have friends who will fuck anything that moves, pursue that goal with reckless abandon, and don't care that half of their female acquaintances don't care for their company as a result. They obviously put far more weight on the successes than the failures. Taken to an extreme, this is the "99 slaps" approach, and for some people it is perfectly acceptable. I, on the other hand, would rather have lunch with half of those 100 girls than sleep with one of them. If I ever found myself in a situation where I was completely disconnected from my existing network of friends, and had nothing to lose, I might give this approach a try. "Nice boots, wanna fuck?" is, after all, a quite effective pickup line in a small subset of situations.
Many times, even when I've decided to "go for it", my approach is too soft or indirect. I've been told that I need to be more direct, and I'm trying to do that. Maybe the signals I'm sending aren't getting through. Maybe I'm misreading the responses. But once it's gone that far, the danger of trying harder is increased. I don't ever want to be "that guy who can't take a hint". So far I've only ever been brutally blunt, on the subject of advancing a relationship, once, and that ended badly. I don't know where the middle ground is. The thoughts I am trying to get across could fill volumes, and a simple "Do you want to come back to my place and cuddle tonight" is both awkward to work into a conversation and quite inadequate in conveying my thoughts (in either direction, as that particular sentence can convey significantly more or less intention than it is meant to).
Unfortunately, there is also the matter of effective consent. I'm not comfortable with being intimate with someone who is noticeably drunk or high or whatever else, who has not shown any signs of affection when sober. I know that this goes against thousands of years of social custom, but it isn't a line I'm willing to cross. I've been trying lately to be more direct about following up on this afterward, but it is both awkward and difficult to arrange sometimes, particularly when I never see them sober.
It doesn't help that I've had an exceptionally unusual life, with regards to the opposite sex, before becoming romantically / intimately active. I've spent more days and nights than I can count surrounded by [nearly] nude female friends, either platonically sharing a hotel room or assisting with costuming / modeling gigs, which served as probably-too-strong dont-be-creepy training. I was tying girls up, occasionally beating them raw, and often driving them to orgasms so intense they begged me to stop before I had my first kiss. My first date was unintentional, with someone quite out of my league, both sexually and romantically, and ended quite poorly due to my ineptness. I've spent more time at third base than at first, and with more girls, and am not sure how to go about reversing that.
Overall, I'm looking for advice on how to better to approach women that I encounter on a regular basis, whose company I enjoy and would like to be around more, to whatever degree is possible. I'm not really looking for pickup lines or direct assistance with making connections (although that wouldn't be unwelcome, it's the subject of a different conversation). I need to know if my thoughts on negative consequences are unwarranted or disproportionate, or if there are other aspects of my take on this situation that seem out of kilter to any of my friends here. Hopefully one of you who have read through this post will be able to help. Constructive suggestions or criticism are welcome, admonishments less so, and derision not at all.
PS: There is little more disappointing that being asked by an attractive smart girl, with whom I've been acquainted for quite a while and tried to send all the right signals to in every way short of clubbing her to drag back to my cave, some version of "Your new roommate is hot, is he single?". Thrice. :(
1: I have a wonderful girlfriend who completes me in almost every way, but is unfortunately a thousand miles away, and my few other recurring intimate partners are similarly out of convenient reach.
2: There is a girl who I see about 3 times a year, in the widest possible variety of contexts. Dates, intimate nights spent together, meeting her new monogamous boyfriends (throughout the years), in passing at social events, etc. It's a very strange relationship, and every time I see her so much has changed that I feel like we are starting over, and never from the same place. I recently sent her an email (we communicate mostly online), mostly the contents of the second paragraph of this post, and told her I wanted any or all of the above in whatever combination and degree she was comfortable with. She was quite put off, and I'm sure I've ruined any chance for a future relationship with her. I would rather be back where we were before than where we are now.
3: What should have been a night out with friends turned into just us together in search of some fun, a few games of pool, dinner, and conversation, thanks to mutual friends bailing out at the last minute.