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When do you tell the person you're seeing that you'd like to be exclusive? There are no easy answers, and we're not pretending to have them.But for some nuanced insight, we consulted relationship expert Andrea Syrtash, author of "It's Okay to Sleep With Him on the First Date," about how to navigate some of the most uncomfortable dating scenarios.Here is the basic scenario: What if you have been long-time friends with a girl for three years and recently you started seeing her in a new light?We already hang out either with a group or alone pretty often. And how do I find out how she feels without making it awkward?In addition to less people in general, it also seems to me that it's not quite as common for people to online date as it is in NYC (that's not an official statistic, just an observation. Last night I had a few drinks with a friend of mine who is trying to get out on the dating scene like me.I could be wrong.) This makes for a smaller pool of fish. We both favor OKCupid, and it occurred to us that we should probably make sure we weren't dating the same people.I feel that in the end, we would eventually need to talk about our intentions because hanging out alone now may feel like a date to me because of my change in feelings, but to her it probably is "just friends hanging out" unless she secretly likes me, too. First, I like the idea of a dating relationship having some friendship history.If a dating/courtship relationship is anything, it should be an amazing friendship.

In this situation, your delivery is just as important as your language, Syrtash said.We did a quick comparison on our phones and sure enough, we had several overlaps in our lists of potential suitors.It's not unexpected: we are about the same age, we live in the same area, and we even look vaguely alike, although she is totally cuter.And if you do hook up, then you have to deal with the “what now?” We asked collegiettes and the experts about what it’s really like to hook up with a friend, what to consider beforehand and how to deal afterwards.Have you ever had a friend gush to you about a new guy--"He's 35, a software developer, and he's really into biking"-- and you're like, "Wait, that sounds exactly like the guy I just went out with" and it's super awkward because it I've talked before about some differences in the New York dating scene versus the Midwestern scene, and now I've got a new one.

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