This is the latest post from our San Francisco-based Date Reporter, Sona. Catch up on her story here.
How about you meet up with me and my girlfriends when we’ve been drinking at a baseball game all day, make polite conversation with my friends, pay for the cab ride back to the neighborhood where all of us live, take me out for another drink, make sure I get home safely, and behave like a gentleman the whole time?
That was my first date, and presumably only date, with Jared*. We’d been messaging casually over the course of ten days; I’d originally responded to his suggestion that we go eat Japanese food in Japantown. Our conversation was sporadic because he was initially slow to write back, and I always try to mirror a guy’s pace of messaging. After all, there’s no need to scare them off before you even meet.
The day of our date, Jared messaged me that he was free that very evening, and that I should text him if I wanted to meet up. Now normally, I never, ever send the first text or do any planning for the first few dates. As I’ve mentioned on my blog, I prefer it when a man takes charge. It makes me feel masculine (and desperate!) to initiate any further than sending the first message on the dating site. My first commandment of dating is “Thou Shalt Not Ask Out A Man, or Even Come Close to Asking Out a Man.”
However, a feeling of impulsiveness, bolstered by a few drops of liquid courage, reversed my usual stance and I sent him a text after the game. Even then, I knew how to play it by saying “I’d really love to meet you tonight, but I’m all the way over by the ballpark.” I added that I was out with my girlfriends and I was dressed in festive San Francisco Giants colors. The next thing I know, Jared was on a train coming out of his way to meet me!
I really appreciated that Jared was such a good sport, making conversation with three chatty too-many-beers-in-the-sun girls, one of whom was supposed to be his date. It wasn’t an ideal first date for anyone, but it sure beat awkward small talk over lattes. Instead, I made him laugh by quoting too many lines from “Coming to America.” When he responded by quoting another line from the movie in a wonderfully awful falsetto voice, I was blown away. At the end of the night, he held my hand, walked me to my door, and kissed me goodnight.
I can’t say I’m still entirely comfortable with initiating, especially on a first date, but I’m glad I took a risk. If all else fails, take the pressure off yourself and have fun. We’ll see if it pays off.
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.