On Saturday afternoon, I got a text message from a reader. Who fine, is also my friend. But still – I was pretty stoked that someone sought me out for dating advice for her boyfriend’s roommate. I was doing something insipid, like moving or standing in Target, when I read the message:
Need a good Wednesday night date night activity in the city…and go! (For C’s roomie. Second date. First date was a concert.)
My response was not faster than lightening only because I am perhaps the worst 31 year old texter of all time:
Why the zero hesitation? I don’t talk a lot about second dates here, but here goes…
Second dates are a lot harder than first dates. A first date, your responsibilities are to be the best version of yourself, be open to the possibilities, and cut your date a bit of slack. But on second dates, unless you’re a zen master who is able to see dating as a series of “I wanted to see you today, I want to see you tomorrow, that’s all that matters,” things suddenly get a lot more real. You find out if your giving the benefit of the doubt paid off; you find out if your first impression was right.
However, second dates totally don’t have to be this way. Too many people get caught up in the “oh hey, that first date was good, let’s repeat that date formula,” contributing to only seeing one side of a person, and only showing them one side of you. So, you’ve got to break the cycle before the cycle begins.
The roomie had pulled off a concert – an experience that is loud, and doesn’t encourage much in the way of talking until after, when it’s easy to focus conversation around the experience. Now, it’s time to throw that on it’s head, and give each other only each other to focus on. Both Zeitgeist and Hotel Biron are reasonably hip places almost no one has a problem with going – they’re not overly fancy, and they appeal to a broad audience – Hotel Biron is a wine bar that also has a great Belgian beer selection, and Zeitgeist is known for its outdoor patio (and given the summer-like SF autumn weather…). Plus, they are quiet enough to hold conversations, close to good food in case the date extends into dinner or snack time, and both watering holes will be busy on a Wednesday night (because for whatever reason, being alone in a bar with a relative stranger is pretty awkward).
Morale of the story: For a second date, do something different than your first date.
As for what to wear…well, that’s on you.