The first time is always the hardest. There’s this pressure to do something daring, and wonderful, and of course, to get it right straight out of the gate. Well, that never happens, so I just try to make a start, any start.
On OKC, my favorite “first date” activity is to grab coffee together. It’s perfect; I bring a book and show up a bit early to find a pleasant spot and get settled. I like to have my coffee already when my date shows up because I hate the “who pays” argument. I know that it’s hard for everyone, because there’s so many annoying societal expectations, so I just jump the gun and get my own coffee. And if they don’t show up, well, no worries. I have a book and now I’m going to have a lovely hour or so reading and sipping my coffee. If they show and it’s horrible, well, I drink my coffee quickly, and then “Well, that was interesting, nice to meet you, bye!” But if it goes *well*, aaaaah, this is the beautiful part. If it goes well, and we linger over our coffee, it’s easy to suggest a short walk, or that we grab dinner, or otherwise extend things.
It isn’t unusual for me to suggest “coffee” as an activity, rather than literally getting a cup of coffee. I often have chai or hot chocolate because my coffee dates are usually in the afternoon and honestly I’ve usually had quite enough caffeine for the day by the time they roll around. I just like the activity of “getting coffee”. I like cafes as spaces where nobody has to host, where I can be social and have reasonable expectation of social backup should I need it. I tend to go to the same cafe for my first dates; they know me there, and give me a hard time when I forget my wallet (this happens way too often). I enjoy sitting alone in a cafe reading, or sitting and talking, or sharing a snack. I grab coffee with my partners, with my coworkers, with my dates and with my friends. It’s a lovely, casual, flexible activity and chance to be social and take a break from our day.
Once I started looking at first dates as a chance to hang out in a coffee shop and have an interesting conversation, they started being a lot more fun. It’s pretty hard to fail when the goal is to have a cuppa and either read a book or have a chat with a new person. I’ve even had someone show up an hour late for a date and still catch me because I was still reading; it turned out to be a pretty good date, despite his tardiness.
Expectations are part of what makes the First Times so terrifying. The “What if?”s are killer. So change the definition of “success”. It’s not “Have an awesome date and meet the new love of my life!” because, seriously, who can possibly live up to that? but instead “Have a pleasant afternoon in a coffee shop.” Success doesn’t have to be huge. You don’t have to own half of New York to be successful. You can work two hours a day and make just enough to get by, and be truly successful. To me, I succeeded if I enjoyed the activity, or learned something. All of the relationships that I’ve had where we broke up? Those were successful. I learned something from each one, and they were fun for a while. That’s success. My marriage didn’t make that relationship a success. Success is a destination, a finale, and I sincerely hope that I’m not done with this road yet.