Hi all! You may know me as a prolific commenter on HarvardFML; this is my new and improved means of doling out relationship advice! Got a question you want to ask, or a situation you want thoughts and advice on? Email me at somedude.harvardfml@gmail.com, and watch this space for my answer! DunsterDiver asks,

I’ve had a crush on this girl for a while, and I think I’m going to ask her out. It’s been a while since I’ve been on a first date. What should I plan?

Well, let’s think about the purpose of this first date. It is not to spend time with this girl. It is to get her to want to spend more time with you. If she says yes when you ask, presumably she’s at least a little interested; the first date needs to grow that interest, so you’ll get to spend more time with her in the future.

The pitch: As I’ve said in past posts, don’t ask, tell. “Let’s go get coffee” is better than “Would you like to get some coffee with me?” The former projects confidence and command; the latter is more supplicant and approval-seeking. It’s subtle, but since this is your first overtly romantic interaction, it’s worth setting a strong tone.

The location: The ideal first date is at a cafe or coffee house. It’s a casual afternoon break, not a sit-down meal. Any of the tons of little cafes near Harvard Square would work well. Tealuxe, L.A. Burdick, Crema Cafe, Cafe Pamplona, even Starbucks or Au Bon Pain, and there are many more besides.

Why a coffee date and not a sit-down meal? First, it’s short. You want to leave her wanting more, which is much easier to do if you allow less time. You need to end the date in the middle of a great conversation Short also makes it easier to bail if it’s going really badly. This is hard to do at a sit-down meal, where you have to finish eating and then pay the check. If you have just coffee, and you already paid, you can make a fast excuse and leave.

The date itself: Once you’re on the date, you need to be interesting for her to want to come back for more. Plan what you’re going to talk about. Don’t script what you’re going to say outright, just have some things to talk about; most people won’t be at their most interesting and spontaneous when they’re under stress. A date is not a job interview, so don’t talk like you’re at one. “Where are you from?” and “What do your parents do?” and so forth may sound like good questions, but they and their answers are usually wooden and predictable, and don’t usually make for animated chitchat, which is what you’re going for. What is good for animated chitchat? Just about anything, especially if it’s unexpected. I read the news every morning, which is usually full of new stuff to chitchat about, and I offer that as a suggestion, but you can talk about just about anything. What you say isn’t nearly as important as how you say it: be funny. Don’t be afraid to be spicy too, as long as you keep it funny at the same time.

Who pays? This is really up to you, but I’d each pay for your own stuff. This is uncomplicated and at a coffee shop, inexpensive enough to be fairly trivial, and becoming more and more common date etiquette anyway. Some women expect the person who did the asking out to pay; some women expect the man to always pay, some men expect that if they pay for their date they should get something in return. Also consider that if you pay this most trivial of expenses for her now, she may expect that you will always pay for her in the future. Broadly I think it just sets a safer precedent for each of you to pay for your own.

The end: End the date intentionally while you’re having a good time. Make an excuse if you have to. The whole process has been leading up to you cutting the date short with some sort of “to be continued.” Letting the conversation run its course does work sometimes, but people with certain personality types are always at a disadvantage if you go that direction, as if the conversation gets exhausted there will be an awkward silence, and you don’t want that to be what sticks in her mind.

Next date? Conventional wisdom says that you should wait about three days to call or otherwise contact her again, but that’s unnecessarily rigid. Don’t call so soon that you don’t give her a chance to miss you, so definitely not the same afternoon. And after more than three days you risk her forgetting about you. But anytime in there is fine. Good luck!

Special thanks to Meow and Some Guy for coming to my defense, and for Mrow and quadling for honest and respectful debate. Email Some Dude at somedude.harvardfml@gmail.com.