This is the latest post from our San Francisco-based Date Reporter, Sona. Catch up on her story here.
Among all the labels you can put on a relationship, the one I hate the most is penpal. While the word “boyfriend” makes me cringe almost as much as “moist,” I am indeed seeking the off-label version: partner-in-crime, gentleman-friend, man-friend, and ultimately, fiance and husband. Nowhere on that list is penpal.
This was my slight frustration with Jack*. We started talking when he intrigued my date idea, “How about we take the Filbert St. steps to Coat Tower and get a drink at Vesuvio after?” Soon, we’d hit the 20 message mark, and there seemed to be no indication of moving the online conversation offline. Instead, we were engaged in a game of message chicken. Most of the messages hovered around small talk: the weather, favorite activities in SF, more of the weather. Topics I could congenially discuss with my mortal enemy or the CEO. They’re no predictor of how we’d actually get along in real life.
Feeling a bit frustrated, I decided I’d just brave breaking my #1 rule of not asking men out by casually suggesting meeting up. I’m normally old fashioned; I expect men to do the asking and me to do the accepting. But after conducting a scientific poll of two straight male friends, 100% of them agreed that suggesting “maybe we could do that hike this week?” was not in fact aggressive, needy, or over-eager. Perfect!
Fortunately, Jack* managed to preempt me and suggest it first! So on the date we went, a weeknight urban hike with gorgeous views, followed by drinks.
The evening was proof that endless messaging is a horrible way to get to know someone. Where the email exchanges were somewhat dry, in person Jack’s intelligence and humor came out very well.
There was the awkward moment during the date when we realized we lived across the street from each other. At the end of the night, I tried to sound as cheerful and breezy as possible when I said, “Good night! Please don’t stalk me, ok?”
Would I see him again? Yes. Will I suggest it? No. Now that we’ve moved offline, the stakes are higher and the ball’s in his court.
Now it’s your turn! Tell us:
Sona is a Midwestern transplant living in San Francisco, where she’s lost her tolerance for cold weather and is attempting to become a wine snob. She works in online advertising, figuring out the best way to make advertising useful and not distracting. She’s a runner, reader, and a pro at spreading out her vacation days to travel the globe. Because we know you can’t get enough of her dating stories, read more on her blog, UrbanCourtship.