How to Plan a Nifty First Date

First date jitters, you know the feeling: that gnawing pit in your stomach eating away at your confidence, making you wish you had never planned a date in the first place. Well what if I told you that you could do away with the dread and actually look forward to your date?  The first step is preparing yourself for the date, but now you have to plan the date. If you plan well, those first date jitters will not be from anxiety but excitement! Here are a few tips for crafting the best first date from my own dating adventures.

Note: These lessons are from my experience and thus lean towards the heterosexual point of view, but I hope these tips can apply to all kinds of relationships!

1) Do something fun: Save the movies for the 3rd date

Going to the movies is a classic date option, but from experience, it makes for a horrible first date. If you are meeting for the very first time, are sitting in a dark room where you cannot talk for 2-3 hours, and feel pressured to hold hands before you even know his last name, you are not in the best context for getting to know each other. Save going to the movies for the third date, when you’re starting to feel more comfortable and you can snuggle—if you play your cards right—on the couch at the local theater pub, drinking a beer and holding hands. I can tell you from experience, this is a great choice for a third date and it is best followed up by a steamy make-out session in the alley next to the theater.

“Do something fun” may seem like an obvious suggestion, but my emphasis here is on doing something. Going to the movies is not really doing something, it’s watching something. Going to dinner does involve eating, but little else to do besides talk. From my experience, the best first dates are when you pick an activity that you can both do together. This allows you to take a moment from talking about yourself and talk about what you’re doing, which takes the pressure off the date and makes it way easier to have fun and connect!

One of my best dates was a night of contra dancing. Yes, instead of dancing with my date all night, I spent the night being spun around by 60-year-old men until I was dizzy, but I smiled the entire time. And when I got a drink with my date afterward, we had lots of hilarious stories from the night to tell. Other great options for doing something on the first date are bingo, trivia (if you aren’t too competitive), or an art walk. The last one is such a good option for a first date that it tricked me into thinking I liked a guy, when actually I only liked going on the date. I broke it off a couple dates later when I realized that I had just planned too good of a date. So good, in fact, that a month later I saw that guy at the same art walk with another girl and when he saw me, he grabbed the girl’s hand and walked away in a huff. And I just thought, “Good job, man. You figured out that this is the best date in town. Go have fun.” And I wish the same for you.

2) Have a time limit.

Part of picking a date where you have something to do is so you don’t spend the whole time talking each other’s ears off. If, however, you end up going to dinner or to coffee or any place where it’s easy to sit there talking non-stop, I suggest setting a time limit. I don’t mean telling your date that he only has two hours to get to know you and after that he must not say another word. I mean know your stopping point. If you’re going out to dinner, have a time you think you should head home. Or if you’re really unsure about the guy, book something after the date. I once went to coffee with a guy and we sat there for three or four hours talking about nonsense, both knowing that we’d rather be somewhere else but neither of us having an out. This isn’t to be cynical and say that you should set yourself up in case the date doesn’t go well, but that you should remember: it’s just a first date. It doesn’t have to go the whole day. If you like each other, you’ll have plenty more time.

3) Offer to pay: ladies & gentlemen!

To pay or not to pay, that is the question—a question that has haunted me at least. There is a scene from How I Met Your Mother where Ted is trying to choose between a girl who he connected with on a first date and a girl who offered to pay. And he really can’t decide. That scene has stuck with me. On one hand, I was raised on the idea that men pay for dates. That is a perk of being a girl, right? On the other, if I don’t offer to pay, will he think less of me? (Thanks, HIMYM.) Or even worse, if he doesn’t pay, is it still a date? I’ve realized over time that these questions are silly. If the date is good, it won’t matter who paid. This wisdom however was learned the hard way:

In my previous article, I mentioned going on a date with a guy who—it turns out—didn’t really think of me that way.  What I forgot to mention was that during the previous “date,” we paid separately. Rebounding from that experience, on another date, I practically forced this new guy to pay. We were again going to a movie and when I stepped up to order tickets, I freaked out. I worried that if I paid, I would be sending the signal that this is not a date. So, I stepped aside and looked at him in a “Now it’s your turn to pay” way. He looked shocked for a moment and then said “Oh, I’ll pay.” The awkwardness was palpable! Luckily, the rest of the date went fine because—get this—it had no correlation to who paid. Unless you are only in it for a free meal, then you don’t need to worry about money, because that’s not the point. The point is to see how well you get along, not who can bank-roll your next holiday.

This is why I’ve now adopted this policy: I always offer to pay. If he says no and then pays, great! (It’s always nice to be paid for.) If not, oh well. As long as you’ve prepared yourself properly and picked something exciting for you to do, you’ll be enjoying the night too much to worry about money. Remember: it’s just a first date. So have fun!

Photo by Sara Slattery
Photo by Sara Slattery
Share on:Share on FacebookTweet about this on TwitterPin on PinterestShare on TumblrShare on Google+Share on StumbleUponShare on RedditEmail this to someone

Leave a Reply