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Yes to close proximity locales. Most began at bars where we sat next to each other.
Any kino would feel forced and creepy.
Conversations about past relationships/bad dates/ funny/horror stories, definitely yes.
Sexual discussions, not a chance.
In fact I dated one girl who said she met a guy recently online who "started talking about all this sexual stuff" and her response was "Whoa! We do NOT know each other like that!"
So ask her about anal sex without sounding creepy huh? :-/
It's not hard to ask about anal sex without sounding creepy. You only come off as creepy if 1) She's not physically attracted to you or 2) you come off as in-congruent. If you talk about anal sex like it's the most natural thing in the world, then she will follow your lead. Usually, I bring up sexually themed topics by telling stories. The progression of conversations goes like this:
-talk about online dating
-talk about funny/terrible stuff that happened on previous dates
-ask her about dating history
-tell story about my trip to a swinger party
-OR talk about why men are typically relationship-impaired
-OR tell her about my experiences in an open relationship
From that point, I can pretty much talk about anything. It's actually a really natural progression and does not come off as creepy at all. Most girls are really fascinated by my more scandalous stories and ask a lot of questions. Kino is also really easy, especially if you're sitting next to a girl.
-You turn away from her to talk to somebody, then you turn back towards her and put your hand on her lower back
-You tease her about something until she acts fake-angry/grumpy, then you say "Awww" and give her a hug. (Ex: "I bet you are trouble, I can tell.. you're probably trying to get me drunk so you can take advantage of me later. I bet you're even planning on stalking me after this" Her: "Hey! Don't say that.. I'm a good girl. I don't stalk people! *fake angry*". Me: "Awww.. you're cute *hug* for somebody who's totally planning to stalk me later" *big smile*)
-You tell her something scandalous so you have to lean in really close to her ear and whisper it to her.. grab her waist while you're doing it.
All your interactions should be playful. Avoid any interview-style questions or serious topics of conversation. Don't give direct answers to direct questions.
-Wolf