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Will Toledo Todd find love in the office?

by Dear Jon
June 7, 2001

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56th Sort_Dear Jon-Will "Toledo Todd" find love in the office? ACTUAL LETTER TO DEAR JON:

Dear Jon,

A beautiful college senior is working at my company in a different department. The nature of our jobs bring us into somewhat frequent contact for brief conversations. She smiles at me all the time and not only does she laugh at my jokes, she GETS them. She is witty and kind.

I would like to ask her out. I am 30 and I think she thinks I'm several years younger. Should I be forthcoming about my age? I don't think age, at this point, is an irreconcilable difference. I have not gone after women that much younger than me before. I seek a second, more disinterested opinion. Thanks.

-Toledo Todd

Dear Toledo,

You would like a disinterested opinion, eh? You have written to the right person. I will present you with only rational advice, because I am, after all, not interested.

When presented with such a set of facts, some might desire more information out of an adolescent curiosity, as though to satisfy some kind of vicarious wish-fantasy. Some might be carried away by the image of a beautiful college intern looking one in the eye with interest and pleasure, giggling giddily at the evidence of droll masculine wit. I, however, am not at all curious. I do, however, need to know a few things before I can determine the best possible advice for your situation.

When you say "beautiful" do you mean like Betty, or like Veronica? Is it a freckled girl-next-door beauty, or a glamorous super-model beauty? Is she Oriental, Black, Central Asian, Middle Eastern, Meditterranean, Central European, Northern European, Native American? If she is white, is her hair orange, auburn, blonde, flaxen, chestnut, brunette, raven? Is her hair long or short? Is she tall, short, or medium? What color are her eyes? What movie star does she remind you of?

Until I know a little bit more, I can only speak in the broadest generalities. On the whole, men who are 30 are not too old for College seniors. She will admire your experience of life, without being so immature or naive about what life brings.

You do not have to tell her your age, however, until after you and she have discovered more about each other. You do not have to lie about it, either. Some facts, like, "How long have you been working here?" "Oh, about 7 years," will cause her to piece together the information. If she asks straight out, you could make it a game. "Guess my age within five years and I'll buy you dinner. You have fifteen guesses." "Um, 25?" "That's within 5 years! Can I pick you up at 7?"

You only live once, so do take the risk. Why not? The worst she can do is tell you to choke and die, charge you with harassment and then take out a restraining order. But there are plenty of other fish in the sea.

Remember, she may just be witty and kind. I have lost count of the number of women I fell in love with simply because they gave me the time of day. So if she makes some lame excuse, like "I have a boyfriend" or puts you off, let it go. Whatever you do, don't turn this into a weird "Dear Jon gives me permission to stalk you" sicko thing.

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Dear Jon Letters: Tips for Dating and Mating
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