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I have, well, a problem. I met this guy on the shuttle and he has been plaguing me ever since. He just doesn't get it. When I said I was busy five times...he asked me on a date. He is a nice enough guy, but he just doesn't do it me. But lastly, he went a bit too far; for he has asked my roommates numerous times whether he has a chance and they have been nice but aloof. How I let this guy know that I am not into him without being mean?
The shuttle as social forum is a uniquely Quad phenomenon, with its own etiquette and protocol. But your problem is fairly universal.
The generic situation: You meet a person in a somewhat random environment (in our case, the shuttle). You and said person have moderately interesting conversation for a finite duration of time (a shuttle ride, of in other cases, an airplane trip, walking from Dunster to the Science Center with a third person, etc.). You proceed to go on with the rest of your day, not stopping to think twice about the conversationalist. He (or she, as the case be) definitely does not forget you and proceeds to either initiate contact with you or your friends to find out more information about romantic prospects.
So you blow this persistent person off. They choose to ignore this response. However, rinse and repeat, as many times as desired, they just won't wash out. Unfortunately, unlike shampoo, clueless suitors seem to be a lot harder to get of your hair.
In your case, that's where the fine line between being rude and being direct comes in. You need to let the guy know that you are not interested, which you obviously have tried doing with limited success. Although you may be the nicest person ever (and it seems like you are, having put up with this so far), you need to be more assertive.
Instead of saying you're busy, be clear that you are too busy to make time for him. Rather saying that you have another engagement, say that you are not are not interested. If you can't bear to do that, say that you have a lot of work or give some other suitably vague excuse such as "I cut my foot earlier and now my shoe is filling up with blood. Gotta go!"
Or alternately, get your friends to do the dirty work for you. After five invites, I think either avenue of action is perfectly acceptable. If you see him or happen to converse with him first, you tell him. If he approaches one of them first, have him or her to do the deed. But establish this policy with them ASAP. The only way he could possibly be upset and justified is if you saw him and didn't say anything and then he saw one of your friends and they told him what was up in the most brutal way possible.
One question you might want to think about: Do you want to be friends with this guy in the long-run? You seem to think he is nice, just rather persistent. Would you be interested in getting to know him as a friend? While this may prove to be impossible given your past history, you should think about it in the way you let him down. But a large part of whether or not you become friends will depend on what you do after you establish that you are not interested in a relationship. And if you do it yourself (instead of involving your friends), you have a lot more control over what happens next.
There are basically two or three scenarios here.
Scenario A: He's extremely mature, you're extremely nice, and you end up being friends (ideal, but often difficult).
Scenario B: He's hurt (wrongly or rightly), you don't make the effort to follow up on your token gesture of friendship, and you end up being "What's up?" friends (most likely).
Scenario C: He's extremely hurt, you feel liberated but upset with him for putting this burden on you, and you never talk to him again (somewhat likely but only for the more melodramatically prone).
In any of these three cases, at the very least, he won't be struggling with the idea that you ore just a really busy person that might possibly be interested in him. And that will, in the long run, make both of your lives a little easier.
Please see Romy and Michelle's High School Reunion
A special note to all of you river people: I've noticed that your lives seem mighty put-together. Or maybe you don't have lives to discuss. Why don't you prove me wrong next week? (and before I get a bunch of e-mails from the House Committees of the river houses, that was just a joke. Don't get too excited).
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