Lest that make me sound totally bitchy and antisocial, let me clarify: there is something about both the concept of dating, as well as the reality of awkward conversations, especially during first dates, that often zaps the fun out of it for me. All the things I like about meeting a new person or having a crush, about geeking out over what I’m going to wear and how it’s going to go, seem to get lost in the concept of “dating.” It sounds more like a dreary, awful job than something I should want to do.
Some of my best dates have been ones where we did something either unexpected or extremely casual. I’m not the kind of girl who cares about all things fancy; in fact, the time my ex took me to Babbo, while it was fun, was not as fun as the time we cooked together. For me it’s much more about the person I’m with than what exactly we’re doing. I like dates that teach me something about the other person’s interests, especially when they’re different from my own, as well as dates that teach me something about mine.
Tamara Duricka Johnson went on 30 consecutive first dates for 30 days as part of a project she writes about in her memoir 31 Dates in 31 Days . The 31st was with one of the previous 30. Just hearing about that premise made me cringe, even though I liked seeing what she planned for her dates, everything from going to the theater to visiting the Central Park Zoo. I admired her stamina in sticking to her plan and casting a very wide net; she met guys via friends, word of mouth, at church and online, and seemed to have a “open to anything” attitude. She didn’t rule out guys because of age or height or career. And yes, there’s a happy ending, though you’ll have to read her book to see how it all played out. Still, I cannot imagine any situation where I’d enjoy going on 30 dates in a row, either with the same person or all new people. I like my alone time way too much.
Part of my discomfort with the concept is that if I’m going out with someone I don’t know well, whether a friend of a friend or an online date, it’s hard for me not to feel like I either need to tell them everything about me all at once or like I’m on a job interview. The things I care about, like how close a person is to their family, what their life goals are, what they’re passionate about, are not usually first-date conversation. That tends to be more of the “where did you go to school? what do you do?” type conversation and that’s just not as interesting to me. I don’t want to feel like I need to bring talking points to a date, and sometimes that means suffering through deadly silence, like the date who responded to my “Where do you live?” question with “The Bronx and Brooklyn.”
That being said, I do like the drama of a date, even though I can find it maddening. It’s exciting to either plot out where you want to take your date, or be surprised at where they decide to take you. I’m a cheap date, and I actually prefer dark dive bars to loud, flashy places, but I’m open to almost anything, as long as it’s something the person genuinely wants to do and isn’t doing to try to impress me. The part of dating I hate most is that sometimes, in trying to put our best foot forward, we wind up putting a false foot forward. We showcase who we think we should be rather than who we are. I dread dates where I can’t read the other person well enough to know what they’re about.
The conundrum for me is that while I’m not actively looking, when I hear about friends’ relationships or online dating adventures, there’s a part of me that’s wistful. I do miss being in a relationship not because I hate being single, but because I miss the process of getting to know someone over time, where you are comfortable enough with them to be yourself but can keep learning about what they’re like.
With one of my exes, we settled into a routine where date night involved ordering the exact same dinner from a local Thai restaurant and eating it as his place and watching a movie. Now, there was nothing wrong with that, and we both had very busy social lives so welcomed the chance to lay low. I was smitten with the spicy eggplant at the Thai place and even though I told myself I should sample more of their menu, I rarely did. Over time, the cumulative effect of all those nights made me feel like we were an old married couple even though we were in our thirties.
I’m well aware that if I do ultimately want to be in a relationship, that will probably require going on some dates first. There are times when I see a location and can’t help but think, “This would be a great place for a date.” Cue Madison Square Park’s food stands. I even have a brand-new dress that I’m waiting for the perfect opportunity to wear. It’s as little too much for a first date, but would be perfect for a second or third.
Okay, so maybe I don’t hate dating so much as get impatient when I don’t trust myself to weed out the bad dates from the good. The last few dates I’ve been on, spanning a hipster bar, a Starbucks, a hotel and a macaroni and cheese restaurant, have been a bizarre mix of public making out, career strategizing, shoe admiration, flirting, a backrub, and someone (okay, me) bursting into tears. They let me get to know the people I was out with through what they said, and what they didn’t and even if I never go on a date with those people again, I enjoyed the unexpectedness of our time together.
I was impressed that when I walked into a restaurant carrying four bags, my date didn’t bat an eye, and in fact seemed enthused by my quirky habit of carrying seemingly weeks’ worth of stuff on me. It’s something I’m working on, but if you can’t handle my (literal) baggage, I’m probably not a good date for you. And I do think that ordering takeout in and watching a movie is a good date, if you’re with the right person. Maybe I need to mix things up and push myself a little into what feels like the Twilight Zone of dating in order to get to the dating equivalent of comfort food. Or maybe I should just wear my second-date dress on a date with myself, and see what happens.