Hi Emily, I liked the title of your post, it sounded like a sportive event, which is actually what the guy is proposing you- an affair for the sport. He’s had a crush on you for a long time but he obviously thinks that the other girl is more suited to him. He wants to enjoy both worlds, and be with you before he’s “officially taken” . Though he’s honest in a way (he could have pretended to fall in love with you and then with the other one after a month, it happens after all), this behavior is still questionable, and shows that he doesn’t care about you. I have to say that from the outside, the proposal sounds a bit outrageous and coming from a not very nice person. I wonder, why are you attracted to him? ( also, see post on being attracted to the wrong person post and an interesting answer post )

But if you feel very much attracted, why not? Maybe you’d like to see whether your charms will be stronger than his calculations, but be careful, there is the danger of getting hurt (whether in your feelings or in your ego), and you can of course forget about your previous collegial  friendship, though again, I don’t know how much it is worth anyway with such a guy.

Well, maybe you can book him in advance for next Easter.  And then he can tell this other girl she's only got four months...

Seriously, I'm not sure I'd expect much from this guy in the relationship department. Just a hunch -- this doesn't seem to me like someone with a huge amount of self-control. It sounds like he tries to set up barriers in his life so that things happen the way he thinks they should, i.e., avoiding you rather than not kissing you. This is a good strategy as long as the barriers stay in place. But if you get serious about each other, just remember that caring about his Christmas date didn't stop him from caring about you.

Nonetheless, you might have a good time. This is hard to know from what you write; if you've liked him seriously for a long time you might be way too emotionally involved and get very hurt. On the other hand he might be afraid of how much he likes you and exaggerating the importance of this other girl. It's obviously hard for me to say, but for you this should be easier to see. As long as you're clear in your own mind about what you want and what is in fact the case, you should be fine... just take care of yourself. And it goes without saying, use protection.

I think the inherent problem with this guy's proposal is that you're probably setting yourself up for failure and rejection. Certainly it can end well, i.e., he decides he was wrong about you in comparison to this other girl, and wants to be with you indefinitely. But what happens when he follows through with his plan to leave? He's in the clear. He was up front with you from the start, and you are left wondering (I would be in this situation at least) "Why wasn't I good enough to make him stay? Am I so unlovable?"

If you truly are interested in a month-long no strings attached involvement, I say definitely, go for it, because it sounds like that's what he intends this to be. If you do go forward with it I also say it'd be in your best interest to let go of those expectations of "changing his mind" - more likely you'll try so hard you'll come off as needy, which is never appealing. How can you really enjoy time with someone knowing that there's a chance you still won't measure up? I'm not trying to sound harsh, I essentially did the same thing so I can identify with that intense, all encompassing desire to be loved. I guess I'm just speaking from the experience of my own mistakes, in hopes you don't have to repeat them for me. Spending the month with him to try to change his mind - I picture it this frenzied month of domestic goddess sex insanity, cooking meals and folding laundry and doing favors and fucking his brains out to prove just how much better you are than her. What happens when none of that works?