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First Date: Planning For Success

Somewhere between deciding that I want to go out with someone and our first date, there is a question that I dread. “So, what do you want to do?” Occasionally, I’ve gone out with guys who had it all planned, who invited me into a narrative they’d already created, but for the most part, the decision is collaborative.

Perhaps I’m a little more anxious than some might be about this, but it does feel like there is a lot riding on our first activity. I don’t want to lock myself into something that requires a couple of hours, for instance, unless I already know my date well enough that I’m sure we’ll have plenty to talk about. Whenever I need a reminder of why this is important, I remember one date which started with dinner and ended with two rounds of miniature golf. We didn’t have enough to talk about to get us through dinner. As we putted brightly colored balls, I watched a young couple, probably in high school, a hole or two in front of us. They were chatting and flirting, he was helping her set up her shots. They clapped for each other when each sunk the last putt. In other words, they were doing a mini golf date right. From inside my awkward and strained version, I vowed, never again.

But all rules are made to be broken, right? Once, I met a first date at a hockey game. It could have been disastrous, even though I love hockey. I worried that our interactions wouldn’t be as smooth as they had been so far, but I went anyway. I was nervous that day, and nervous driving over, but as soon as I connected with my date, I felt calm. We talked and laughed all through the game (I can’t even remember who won). That first date turned into a relationship.

Sometimes, I get hung up on money. It can be awkward to talk about who’s paying for what on a first meeting. I always try to pick places that I can afford, and I speak up if I’m worried about that. More and more, it’s a conversation I’m trying to have early, before emotions are entangled. That way, everyone is on the same page, and no one feels taken advantage of.

In the moment, sometimes I have difficulty remembering my favorite mid-priced places to eat, or the coffee shops I like in different parts of town. To combat this, I’ve made a list. Now, when someone asks me where I’d like to go, I can suggest crepes, craft cocktails, or well-brewed tea.

Familiarity is another perk I’ve discovered in developing relationships with my favorite first date places over the years. Often, I’ll go a little early and check in with a barista or bartender, letting them know I’m on a first date. More often than not, they offer to check on me, or to develop a signal, just in case I’m in distress. I still might be nervous, but it’s awfully nice to feel like I have some backup.

Unless I have a good reason, I try to stick to coffee for a first date. No one expects more than an hour from me, and I can graciously escape if I’m ready to be done, but an hour can also easily turn into two or three if things are going well. It’s not expensive, and there’s plenty of time and space to get to know each other without a server dipping in, or the distraction of a movie, a play, or a sporting event.

On a first date, I’m learning that my entire job is to pay attention. I want to get to know the person I’m meeting. Even if I know him already, I don’t know him in this context. But more than that, I want to tune in to how the date makes me feel. Most of the time, I’m nervous until it starts, it’s a sort of stage fright, but if I can’t relax as the date goes on, I want to pay attention to that and honor my intuition. Too many bells and whistles can make it hard to notice when I’m uncomfortable, or when I simply don’t feel a connection, but it can also make it harder to see the sparks when they start to fly.

In the end, when I’m thinking about what to do for a first date, I try to remember that they are supposed to be fun. Both of us hope that we’ve met someone special, but I can’t allow myself to think about forever the first time we spend intentional time together. Instead, I concentrate on the person in front of me, someone who has chosen to be brave along with me. I set aside all of my hopes for a relationship (or do my very best), and keep my mind focused on that person and the present, one moment at a time.

caraCara Strickland writes about food and drink, mental health, faith and being single from her home in the Pacific Northwest. She enjoys hot tea, good wine, and deep conversations. She will always want to play with your dog. Connect with her on Twitter @anxiouscook or at