It’s especially a no lose deal, because I’m here to catch you if you fall. I feel like breaking into a cheesy '80s tune now.
I love improv too Swimming. Check out my rant here. Good luck with your troupe.
Hey, you know I’ll be here to console you, though here’s hoping you don’t fail…on either improv or with the guy!
Let me just pile on, here. DO IT!
First, I say go for it.
[whisper whisper]But can I put in a…well…ummmm…jaundiced opinion. …he was working as a nanny that summer. I have never heard of a guy being a nanny before. Call me sheltered, but my life experience is just screaming out (and I’m going to get bashed for this)
“He’s gay!”
Not that there is anything wrong with that…
I seem to remember another post about him…or I’m just going insane.
Anyhoo, I say GO FOR IT, you don’t have much to lose but a LOT to gain!
Good luck!
Swiddles, sweety,
What are you thinkin’ girl? No-brainer. You write him lickedy-split. He will be nothing but flattered. Trust me.
Worst case scenario, you guys have a friendly catch up. Best case? Do I hear wedding bells? Or at least some serious lip lockin’. Do it. Your only regret is that you didn’t sooner.
.b
Yea, I have. I don’t remember where, but I have.
And if he IS gay, I can’t say I’d be suprised. But at least I’d know it. I HAVE heard him speak about girls in a manner that suggests heterosexuality. But hey, I’m in theater. Nothing suprises me. And for the record, I volunteered at a preschool and knew quite a number of heterosexual men. Why would a gay man be more apt to be good with kids than a straight man? Better with interior decorating: yes. Better with kiddies: not always.
I don’t think it’s romantic, or stalkerish. A ‘How ya doing’ Email to keep in touch with a potential partner is just prudence.
Definately do it, but don’t get your hopes up too high – he’s had plenty of time to have a whole bunch of life. He might be married, with kids, by now!
Swiddles, by all means go for it. The fact that you still remember him fondly may jump-start affection on his part.
And I strongly disagree with your pal. Do not bring other people into this. You are the one who wants to hook up with him; don’t distract him.
Maybe. So? Worst case scenario: What you thought was a light, charming, “So whatcha been up to?” email elicits an outright rejection note from homeskillet. So you grab your cat and some chocolate, and instruct the butler to inform any callers that “Ms. Riddles is in seclusion in the East Wing.” You’ve lost nothing, except perhaps, temporarily, your vice-like grip on dental hygiene.
On the other hand, he could email back, what once was merely hope may be supplanted by an even sweeter reality, and y’all could move to the South of France together.
I believe your path is clear.
Do it!!!
Not even close to stalking. Take the chance and roll the dice.
Oh, I absolutely think you should e-mail him. Nothing new from what everyone else is saying, but I don’t think it will be at all obsessive or stalkerish. I randomly e-mail people all the time - “You have red toenails too? Awesome!” for example. In fact, I ended up dating my cutest, most wonderful boyfriend to date in a similar way. Well, actually I got his e-mail addy from a friend, so it was even a little worse…But we ended up very happy for a few months.
Just hurry up and do it. Get it over with!
Best of luck. I’m sure you’ll slay him with your wit and beauty, but I’ll be sending good luck vibes to Vermont anyway. 
I am with the rest of the board GO FOR IT. You dont want to come up years from now and think why didnt I email him? Something good might just come out of this and it is a chance you should take. I did and to this day I am glad that I did.
But make it a personal email. It can still be “friendly”, but definitely don’t send a group email. Guys are obtuse, and sending a group email is just one more potential bit of confusion. (Ok, maybe I’m just projecting here but my advice still stands.)
Good luck!
Just Do It!
Damn… gotta send another royalty check to Nike for that one…
I’m with every other poster in this thread,
“go for it!”
What do you have to lose?
Nothing.