I need a good first date agenda. Can you help?


throwaway88008 asks:

I got a live one here and I have a feeling that if I suggest coffee it’ll be a let-down.

Any good plans in your back pocket?

Demetrius says:

There are a few ways to make a date memorable. Either spend a lot of money on the activity/meal/drinks and go that route, or go for a well planned date. Think of it like paying to go to a theme park, versus planning a nice day at the park. You either pay for your fun, or plan for your fun.

Your basic back-pocket go to plan for first dates where the cost makes it memorable are simple. Fancy dinner at a great place, fancy cocktails, maybe go see a show of some sort. You might be spending several hundred dollars on that date, but it’s a solid go to. With that said, doing this will set the precedent that your dates are memorable because of the cost. I wouldn’t necessarily discourage you from ever doing the standard date, but save it. As for cheaper but still memorable dates, here are a few that I like:

1. The Draw date. No, I’m not actually saying that you should draw your date, (though I’ve done it on a first date and that was a ton of fun) what I’m saying is that you take them somewhere that would draw them there. Whether it’s a bar with a cool cocktail menu, or going to see a specific place or person that they’re interested in, a cultural experience, what have you. This could be a high cost date, if the draw is high cost like going to see Hamilton, or dinner at a Michelin star rated restaurant, or it can be low/no-cost if the draw is something cheap or free. A great example specific to New York City would be walking the Highline as the main draw of your date, or a gallery tour in the Lower East Side, doing a cheap food tour in Jackson Heights, a walking tour/scavenger hunt in the West Village, and countless other options. The main test of whether or not your date is a draw date is asking yourself, and maybe even your date, if they’d go do or see this thing if it wasn’t a date.

2. Coffee, with a twist. The coffee date, while personally not a favorite of mine, is still a popular enough first date option that I can’t disregard it wholeheartedly as a first date option. That said, planning to sit down for an hour and consume coffee and just talk sounds like a terrible idea for a date. This is why I like suggesting Coffee with a twist. The twist is not whiskey, the “twist” is starting with coffee then following it up with something that is actually fun. Coffee then…maybe a walk in your favorite part of time? Coffee then…a trip to a museum? Coffee then…maybe a game of Frogger at your local bar that is also an arcade (Shoutout to Two-Bits and Barcade for allowing both of these options to be possible). If you do coffee then add a twist, your date is going to remember the twist, and not just the fact that you brought them to a Starbuck’s to woo them.

3. The Packed Agenda. While the draw date is all about quantity, and the coffee with a twist date is a blend of quantity and quality, the Packed Agenda date is all about quantity. The thinking here is, that a lot of dates are just straight up mediocre. Still though, if you have multiple activities in a date, even if half of those events suck, you’ve still got another half of the date that went well and that’s what they’re more likely to remember. The most packed agenda date I’ve ever planned was when I was 23 years old and kind of broke, as many 23 years old are in NYC. The date plan was this: Meet up for dollar dumplings and sesame pancakes in the Chinatown/Lower East Side for a light, cheap dinner and to put a base in our stomach for all the drinking I had planned. Next, stop over at a gallery opening in the LES for general cultural reasons and free cheap wine. Then, head over to one of my favorite bars at the time for $4 dollar shots. Next, another gallery opening for more free drinks. Finally, drinks at a bar with a specific draw (it was a “speakeasy” with a hidden entrance).

Just so you know, that Packed Agenda date actually cost me something like $40, total, and it was a 6 hour date. It’s not really about the money you spend when you try to mix it up with non-traditional dates so much as it is the planning you put into it. You can make it about the money, but you don’t have to. If you’re planning a draw date, you should make sure the draw in question is something that your date will be interested in. I’ve got a broad set of interests, so a museum date sounds just as good as a picnic date, or even attending a minor league baseball game on a draw date. That said, not everyone feels the same way, so you have to gauge your date’s interest in whatever draw you propose. Same goes for coffee with a twist dates. If you’ve got a packed agenda, avoid unnecessarily packing it with things just because you can. You can find a balance between a busy date agenda that you’re both interested in versus just having a lot of activities on your date. The date I described was a date I took an art student on, hence the multiple galleries. It wasn’t just because I knew the gallery opening were happening and they’re would be free boxed wine, it was because of those reasons plus I knew that my date would enjoy doing all those things.

No matter what you decide, remember that the planning of a date is the hardest part. If you’re going for a draw date, either check to see if they’re interested, or if you’re going the surprise route have a backup plan in mind. Besides that, remember that planning can help make a date better, but what will really matter on the date is your chemistry and connection.

Good Luck Out There.