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Relationship Health Message Board

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Good luck, EV--you're clearly an unusually intelligent and thoughtful guy who has given this situation lots of careful consideration, and it seems to me that the potential benefits outweigh the risks. Only you can make that decision for sure, but for what it's worth, it sounds like there is a pretty good chance that she's interested in you as more than a friend the way she's frequently hugging you and invited herself over to your house once she heard your parents would be gone. I was a lot like this girl, from the sound of things, when I was a little younger and closer to your age--I absolutely loved sex, was open and uninhibited about it, and I was eager to experiment with a variety of guys. I often flirty with my male friends and enjoyed casual hookups, but I'd also pursue certain special guys if I thought they'd make good partners...I had two really serious boyfriends before I entered college, and while things were good with them, they were very intense and gratifying. In both cases, we started out as friends and gradually hung out more and more, then started hanging out alone, and fooling around led us to fall in love and have very serious (for that age, anyway) relationships until I broke them off after several years each. It's interesting and somewhat unusual that your attitude toward sex and emotions is in line with what people consider the stereotypically female view and that your girl's attitude is stereotypically male, but I don't think this is all that uncommon nor does it pose a serious problem. It sounds like she is willing and able to be committed and faithful when in a satisfying relationship, and I think you two could be very happy together. It's actually good that one of you is more sexually experienced and aggressive...that should balance out well. With both of my first two serious exes, I was the one with considerably more experience while they were virgins, and I was also the one who took the lead when it came to sexual experimentation while they were considerably more active than me in advancing the emotional aspects of our relationships. In my experience, while some people who are uptight, repressed, or unhappy may judge girls who like sex with different people and don't feel obligated to always be committed to their partners, it's the judgmental people, if anyone, who are actually bad people. If anything, women who are sexually confident and assertive are more upfront and honest than girls who pretend not to have sexual needs just to conform to societal expectations. In any event, I've had quite a few serious boyfriends (and a number of friends with benefits or more casual relationships), and I have yet to come across a guy who wasn't surprised and delighted to be with a woman who enjoyed sex as much as they did and didn't hesitate to take initiative and express her desires.

I think you will be equally happy if things turn out well with your coworker, and I certainly hope they do! I have a feeling you might definitely get a better sense of whether she wants more than friendship when the two of you get to spend that night alone at your house. If she doesn't give you an obvious physical or verbal indication that she's interested in you, I strongly suggest that you bring up the possibility of getting romantically involved in a casual way, putting as little pressure on her as possible. You should then be able to get a clear read on her feelings about that idea, though you must be sure to evaluate her response objectively and dispassionately rather than seeing what you want to see and ignoring signs to the contrary. I definitely think that this sounds promising, and especially since you're so young, you'd be wise to go for it while doing everything you can to guard against any awkwardness between you guys if she were to say no to your advances. Even if she does though, I highly doubt that it will end your friendship or even put a major, lasting strain on it unless you allow that to long as you continue to act normal and friendly around her regardless of whether anything romantic develops, you should be fine. As long as you are prepared for every possible outcome, when it comes to matters of the heart, I think it's always better to take a calculated risk than to sit back passively wishing you had the nerve to act and later regretting your failure to take advantage of a great opportunity with someone you really like. One way or another, if you take a chance on her and handle it tactfully, you shouldn't have anything to lose, as you can still stay friends and coexist peacefully as colleagues. And if things go well, then you have the potential to gain a girlfriend, a lover, and a closer friend all at once, which I bet would make both of you very happy. If you do start a relationship, I have little doubt that she’ll care about you enough and be happy enough with you not to have motivation or reason to stray…if she’s anything like me, she’s perfectly happy being faithful as long as she’s in a fulfilling, committed relationship. And in any event, anyone can end up cheating or betraying you…that’s no reason not to take a risk on someone you really like, especially since she’s probably a wonderful lover who can teach you a great deal about pleasing her and women in general. I think your odds are pretty good and that putting your heart on the line here has a much bigger potential upside than downside, so I hope you go for it and succeed—I certainly wish you the best of luck regardless! :)

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