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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.

(For the record, we also determined that while we are a 72% match for dating, we're only a 55% match as friends. ) We cracked up as we scrolled through our lists of matches, but it is kind of strange to deal with! More situations with friends on the dating scene: OMG, My Friend Taught Me the Easiest, Most Effective Way to Meet Guys*[Breaking News From the New York Times: Men and Women Can be Friends!

A few lighthearted rules if you're in a similar situation: Have you ever had this situation with a friend? ](/sex-love-life/blogs/smitten/2012/04/breaking-news-from-the-ny-time.html)Would You Tattle on a Cheater If Your Friend Was the One Cheating?

Read on for Syrtash's top tips on dating with confidence. Would you be open to going out for a drink with me?

" Before you extend the invitation, Syrtash recommended looking for a ring or any other indicators that the person is currently unavailable.

And if you do hook up, then you have to deal with the “what now?

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.

“[Hooking up] can be a natural progression to a long-term relationship, but it can also be the basis for misunderstandings and a lost friendship,” Greif says.

“Are [you] willing to risk what will most likely be a profound shift in the relationship?

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.

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