Friday, February 03, 2006

Looking for Touble

Looking for Trouble wrote:

Dear Cassandra,

Months ago when I found out who my ex (Blake) was dating I looked him up on a popular dating Web site because I knew that’s where they’d met. This is the guy that Blake told me he was supposedly in love with. Well, I had my suspicions that they were no longer involved...only to be confirmed when I saw the boyfriend's (Clay) profile on the Web site.

So one night about a week and a half ago I came home drunk and devious so I sent Clay a “wink” on the aforementioned popular dating web site…which is simply the equivalent of letting someone know that you think they might be cute, but not enough for a full out e-mail. Clay e-mailed me the very next day, all about how he’d just moved (hours earlier) back up to his hometown of Harrington, Delaware after more than a decade of living in the city. I, deciding to be even more devious, began a dialogue with him over the following days. We’d e-mail maybe once a day, and I was asking questions of him that I might not normally ask because obviously I was picking for information, seeing what he’d say.

So it turns out that Clay is definitely a nice guy, pretty funny actually. He doesn’t even mention Blake in his short list of “ex’s”. We did, however, talk on the phone a couple times and he mentioned that he used to dog sit for his “friend” Blake. So I got all the info that I wanted and then some. But now he’s coming back to the city for a visit this weekend and really wants to get together. We’ve talked a few times and exchanged quite a few e-mails. I just don’t want to be a complete $#!% and just not respond to him. Normally I’d have no qualms, but he really is a nice guy.

So my question is…how can I let him down and not see him without either revealing why, or giving him a shot to his ego? Also, is there any scenario where I could actually hang out with him, get to know him a little, and not have it backfire big-time?

Yours Truly,

Looking for Trouble


Cassandra replied:

Dear Looking for Trouble,

How incredibly "Melrose Place" of you. Amanda Woodward would be proud. This is a potentially messy situation. It is only human to want to know about who your ex is involved with, especially when he made a point to tell you all about how happy he was in his new relationship. If you want to play it safe and avoid any chance of either your ex or this new guy finding out about where you fit into the picture, I might advise that you tell him that you are actually out of town this weekend, so you won't be able to meet up with him. If you do decide to meet up with Clay, you need to be absolutely 100% certain that you want to get to know this guy better because you feel a genuine potential connection, and not just because this will give you a better glimpse into your ex-boyfriend's recent love life or because you will be getting back at your ex. If that is the case, you stand to really offend Clay. You also want to avoid any chance that he might mention you to your ex. After all, it is plausible that they maintain regular contact with one another. My opinion is that overall there is very little chance that this flirtation with your ex-boyfriend's ex-boyfriend can lead to a long-term fulfilling committed relationship. There are also so many other people in New York you could meet and find attractive and sleep with that would not entangle you in such a messy potentially emotionally volatile situation. But if you feel an intense connection with this guy and feel a need to explore it and can actually separate him from his past with your ex, perhaps you can give it a shot. But proceed with extreme caution. After all, this guy is completely unaware of your past with your ex, and thus he stands to be hurt should things be revealed. Besides, didn’t you say he lives in Delaware? Regardless of where you live, I doubt you will desire to make frequent visits there.


Looking for Trouble replied:

Well put, Cassandra. Ultimately, the further along I take this, the stronger the possibility that my original agenda is revealed. Clay is definitely nice and certainly cute, but overall I’m not THAT interested in him and he lives in Delaware.

I guess I’ll say I’m out of town unexpectedly for work…ugh

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Cassandra darling, what's wrong with a long-distance relationship between New York and Delaware? I know it's a little far, but it isn't like the guy is in *Austin, Texas* or anything...

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