5 Tips to Plan Jaw-Dropping Dates

I don’t like to toot my own horn, but I know how to plan absolutely incredible, Jaw-Dropping dates.

Okay, I lied. I LOVE to toot my own horn.  I know how to Plan absolutely jaw-dropping, amazing dates and I’m proud of it.

Now, I want to teach you how to do it.

But first, some info and caveats.

You don’t need to be a baller to plan an amazing date.

In fact, what people typically associate with awesome dates (i.e. spending a ton of money) is actually going to work against you most of the time. Unless the person you’re dating is massively superficial, an overly expensive date will probably make them uncomfortable, especially if it’s a first date. A Jaw-Dropping date happens because of a few things, but the money spent isn’t the biggest thing. It’s how fun the date is, how interesting or unique the date is, and finally how good the company is. No matter how cool a date is, if you guys don’t click then he or she wont be wowed. Just keep that in mind.

Now, here’s  how you can learn to plan jaw-dropping dates.

1. Do Your Research

I’m tricking you into actually working but listen, you need to do the Research if you want your dates to go from “Average” to “Undies-Dropping Awesome“.

You need to do some research the type of person you’re going on a date with and what sort of interests they have. I’m not saying that you need to sit them down and grill them, just get a good idea for the types of places and activities that this person likes. Do they like dives with cheap beer  or are they a cocktail bars type of person?

One of the best planned dates I ever went on cost me $40 but was Awesome. The girl was an art student at SVA who was new to NYC and at the time I was pretty broke. So what did I do? First, I plan a date consisting of cheap eats in Chinatown (Prosperity Dumpling FTW!) then do a little walking tour of the Lower East Side where I highlighted interesting facts about the neighborhood and it’s history (immigration, crime, tenements, graffiti, and so on which I knew about because of all my research) and from there for drinks we went to a gallery opening where the art was so-so but the free wine was awesome. After this, we went to see a documentary on…something Artsy? (Can’t remember, it was a LONG time ago). Anyway, the date cost me about $40 bucks ($13 movie ticket x2, 2 orders of $2 dumplings, tipping the server at the gallery) and the girl was absolutely impressed with the date because it catered to her interests.

I think she would have been less impressed and felt a little uncomfortable if our first date was at an expensive restaurant where she couldn’t split the bill even if she wanted to. On the other hand, there are girls I went on dates with where if our first activity was $2 dumplings that date would have ended then and there.

It’s all about knowing your audience and catering to that audience. Once you’ve done that, do some research on date venues you think they’d love. If you don’t go out much, do all your research on Yelp. You’ll get a feel for the place (plus you get pictures!)

When you’re floating your date idea, if they  express anything less than excitement, think of something better. A lot of what makes a date Jaw-Dropping is the anticipation of the date. If they come into the date excited about the venue or the activity, half of your work is already done.

Sometimes that excitement comes from the new and unexplored but sometimes it comes for a personal favorite. Remember, just because it’s a first (or second, or third) date, doesn’t mean it necessarily has to be a new place. It’s all about knowing your audience.

2. Be Flexible Or just Overplan

I’ll admit it, I tend to not be a very flexible person when it comes to dates. In fact, what I tend to do is Overplan dates. Instead of planning  for just Option A, t I also have an option B, C, and D. If you’re a rigid planner, but don’t want to appear rigid, just make multiple plans andonly share the one good plan. Alternatively, if you hate planning but dont want to be unprepared, just do some really basic research as simple as where are the nearest alternate date location options.

You’ve already done the research and you’ve learned all you can about the person you’re going on a date with so be confident in your plans, but also willing to bend a bit.

3. Don’t Push the Agenda

You may have planned an awesome 8-part date, but if you’re on part 1 and it’s going well, just live in that moment. If part 1 is absolutely killing it, don’t force part 2 (or 3). A date isn’t a thing that has to follow a script, it just needs to be fun. Just because the example above had multiple parts doesn’t necessarily mean that all of the dates you go on should have several parts. I’ve had amazing dates that had one part and I’ve had terrible dates with multiple parts. It’s not the quantity, it’s the quality.

Don’t rush ahead j on a date, be happy with having planned a date so good, you couldn’t get to everything you planned.

4. Don’t Plan an End

This ties into the Not Forcing It idea of step 3.

If you’ve planned an end, there are certain limits that you’ll apply to yourself.

If the person you’re taking out has an end time in mind, that’s totally fine. Just make sure you don’t have an end in sight. Some of my best dates happened because I said “Screw it, lets keep this going”. If you limit yourself to a timeframe, you’ll probably rush your conversations, spend a good amount of time watching the clock, and come off as not wanting to be there.

Now, don’t blow it by saying that “This Date Has No End Time!“. Just don’t mention it, and let things end naturally.

5. Timely Follow up 

Nothing kills all good will you’ve earned from an awesome date quicker than doubt. “Did they have a good time?” or “Are they still interested?” will absolutely kill what chances you had of a second date. Whether you call or text, be sure to follow up promptly.

Here’s a good rule of thumb: If you think the date went well, text or call at least 6 hours after a good day date, or the next morning after a good night date. Avoid calling or texting during prime Drunk Text hours (11pm-5am) and you’ll be set.

That first follow up doesn’t have to be the point where you plan the next date. Just thank them for their time, reiterate how great of a time you had, and tell them when you’d  (roughly) like to see them again if they’re interested and free.

ex.: Thanks again for an awesome time last night! If you’re free next weekend I’d love to take you out again.

What’s the point? Well for starters, you can always have great dates with people who don’t want a second date. That communication gives them an out. It also sets up the next date if they are interested and you get the chance to plan another awesome date.

If you do your research, remain flexible, don’t rush things, and follow up you’ll be planning Jaw-Dropping Dates in no time.

…and as always, Good Luck Out There.

4 thoughts on “5 Tips to Plan Jaw-Dropping Dates

  1. Pingback: I’m Clueless about First Date Etiquette! | Tao of Indifference

  2. Pingback: How You’re Ruining Your First Dates, and How To Stop | Tao of Indifference

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