MT: Do you frequently have problems with guys barking up the wrong tree? If so then what, if anything, do you do to nip the situation in the bud.
Jenny: Unlike a lot of girls, I think my personality is naturally very easy to read. If I'm not interested, a guy usually figures it out rather quickly.
MT: I dunno, some guys are pretty dumb.
Jenny: Not the ones that I date.
MT: Hah! Well played. So what's best way for a guy to make his intentions known without getting put into the 'friend zone'?
Jenny: Be direct about what you want. That doesn't mean asking for permission to give someone a kiss. Frankly if a guy ever did that to me I'd flick him in the head. Sometimes it's appropriate to make your intentions clear by stating what you're looking for in the natural flow of a conversation, but whatever you do, have some balls and if you know what you want, don't be afraid to pursue it.
MT: So always go for the kiss on the first date?
Jenny: The only right answer to that question is 'it depends.' Women are not some monolithic entity. Adapting to the situation is the key. If the woman is clearly not into you, don't force it.
MT: And what's the easiest way to figure that out?
Jenny: There's a couple signs you're looking for. One is how many questions they ask, and their general level of curiosity about your life. Then there is physical contact. If you try to initiate any hand holding, wrist touching, waist wrapping or any other mildly subtle gesture, how do they respond? Do they reciprocate? Do they give you a dirty look or recoil in horror or do they allow the contact to continue? Lastly, and this is a big one for me, is the level of enthusiasm of my answers to the questions a guy might probe with. Generally the more excited I am about a guy the more I'm excited to share things about myself with him.
MT: And if you're not into him?
Jenny: You mean other than I will probably cut out on the date early?
MT: Ouch. Yes, other than that.
Jenny: Short answers, no questions, and there's a perceivable change in my body language, arms folded, etc... I might even rearrange the glassware on the table to prevent him from physically reaching across to initiate contact.
MT: Wow, that's kind of fucked.
Jenny: Why is it fucked?
MT: It's like your building this castle of impenetrability around yourself.
Jenny: Exactly.
MT: Hah... ok so last question. What's the quickest way for a guy to start getting more dates?
Jenny: The thing that amazes me is how often a guy feels like a woman is out of his league. I think guys miss out on a ton of opportunities because they make poor assumptions about who may or may not be into them. Just take a stroll through central park and see how many short guy / tall girl couples are walking arm in arm. You really never do know until you ask.
MT. Good stuff, Jenny. I'm sure all our readers will have appreciated it.
Jenny: No problem. Glad to have helped.
MT: Oh, and one last thing. Think I could get your number so the next time I'm in New York I could give you a call for a drink?
Jenny: Do you really think you're in my league?
MT: Point taken.
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