Should I send him off?

Iced coffee, Love Letters, GChat, then breakfast Skittles.

Hi Meredith -

First off, I've been an avid follower of your column since last summer. My day often starts off with an iced coffee and a GChat message from my friend down the hall asking if I've yet read today's Love Letter.

So, let me cut to the chase. I'm a single, 25-year-old gay male. I have a good job, great friends, and an active dating life. I’ve definitely had my fair share of discouraging dating situations, but at the end of the day, I know that I’m young, and try to be as realistic as possible in terms of the trials and tribulations of singledom, so to speak.

Recently, I went on two great successive dates with this guy. He’s smart, funny, successful, ruggedly handsome, earthy-crunchy, etc. Here’s the dilemma: he’s moving across the country. I knew he was moving before our dates, but I didn’t see the harm in getting together. I didn’t expect, however, to make such a strong connection with him. Now, he has invited me to join him for a leg of his cross-country excursion. A huge part of me thinks that it’s totally crazy, but another part of me wants to embrace some type of cliché motto, i.e. “you only live once” or “carpe diem.” I mean, is there really any harm in joining him if he wants company?

Also, for a little background, I’ve only had one serious boyfriend before. We started dating in college, and continued dating after graduation, although he lived in New York and I lived in Boston. Ultimately, we broke up, mostly because of distance, and since then I’ve been of the mindset that long-distance relationships never work. So, with that said, am I totally crazy to travel with this guy? At this point in my life, I’m ready for a real, meaningful relationship, and given my history, am afraid of having long distance "convenience" relationships be a pattern of mine. Am I overthinking this?

– Single in Somerville

First off, thank you, SIS. My day also starts with iced coffee and some GChatting about Love Letters. I'm self-centered like that.

I'd go on the trip, assuming you feel safe alone with him. I'm not promising that the drive will be so fantastic that he'll turn the car around and shout, "You're too good to leave!" But I do think that time in a crowded vehicle will clarify whether he's worth keeping as a long-distance "friend." Maybe he'll turn out to be annoying in large doses.

I'm not a fan of long-distance relationships, but I am a fan of keeping in touch with someone who has potential. This thing is new enough that you can take the ride and find out whether you like him more (or less) without putting too much on the line. Maybe you'll eventually settle in the same place. Maybe you'll become close friends. Maybe you'll date a bit until one of you wants to move. At the very least, you'll get a story out of it -- "The time I drove across the country with a ruggedly handsome man who became a movie star on the West Coast." (In my fantasy, he's an aspiring actor moving to Los Angeles.)

I know you're trying to protect yourself from getting attached to someone who's leaving, and from having a long-distance relationship that's all too casual, but don't jump to conclusions. You're young. You're looking for new experiences. I give you permission to gas up the car.

Readers? Am I wrong? Should he plan to motor west? If not, why? Discuss.

– Meredith