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  • Oriana Skylar Mastro

Planning Fun and Memorable Date Nights

I love romantic comedies – the worse, the better. I love the falling in love montages. Before officially dating, the couple finds themselves accidentally on a date, riding bicycles through vineyards, chasing each other through fields and urban parks, experiencing an amazing show, sharing street food. I could go on and on.


This is only one of the unrealistic tropes romantic comedies fill our heads with – dates spontaneously happen. I mean, maybe. But, like, where did they rent those bikes? And how did they know those hot dogs would be good? How did they manage to get last-minute tickets to an amazing show or reservation at a top restaurant?


Memorable leisure requires planning - and we should put in the time. Laura Vanderkam, in her excellent book I Know How She Does It advocates for planning leisure time on the weekends as much as we do so during the work weeks. - or else we waste our free time just trying to figure out what to do. Additionally, many studies say that date nights are the key to happy marriages. Apparently anticipation of the event makes us happier than the event itself, so planning, in this case, should bring us some joy!


To encourage you to embrace planning, here are some ideas on how to approach date nights (or nights out if you happen to be gloriously single right now).


1.Pay the setup costs.


My best friend’s parents, a couple I admire, went out every Saturday night together. I remember because we 'babysat' her younger siblings, which just involved eating pizza and watching A League of Our Own for the hundredth time. Anyway, they swear by the weekly date nights. So I decided when I got married, I would do the same.


Setting up a weekly date night takes the decision out of the equation. You are going out every Saturday night (I prefer this to Friday when I'm usually so tired I can't even be bothered to watch the next episode of 'insert show here). End of discussion. You'll be happy you did.


For those with children, this involves finding a babysitter than can come every week. Of course, there is a week here or there when something comes up, but finding someone who can more or less commit to coming by every week creates stability for your children and minimizes the admin you have to do to plan your date nights.


The next question is, what should you do? My husband and I have tried different approaches to date nights over the years. We've taken turns planning. Sometimes we planned the perfect date from our perspective (and the other person 100% has to go along with it enthusiastically). Other times, we plan what you think the other person would love. Lately, I've done most of the date night planning, but that's just because I like taking breaks from work to browse fun and crazy options.


There are several places I get inspiration. Always, always, always ask friends. Also, I may be old school, but I love the going-out guides of the local newspaper. When I lived in DC, I loved getting my Washington Post and highlighting the shows I wanted to see, restaurants I wanted to eat at, and the exhibits I planned to attend. Each city I live in has different authoritative websites with reviews (though Time Out is a good go-to). Searching ‘unusual date night’ in your city usually yields some fun results. I also scourge the voucher websites (travel zoo, living social, Groupon, Viator) for good deals for events and activities, which has led to nights of pottery, painting, high teas, boat tours, small live concerts, to name a few. Finally, if you know what you like, become a member of a museum or get season tickets. There are several financial benefits to doing this (esp for theaters that have black Friday/Cyber Monday deals).


2. Put it all together. You are going to want some way to organize all date nights idea you gather periodically. I use pocket – it is super easy to clip websites. Some I saved this week? Ice skating, a Taylor Swift music night, an 80s themed cruise, rugby games, a list of best wine bars, and a well-regarded Norwegian restaurant.


3. Produce reminders. To score the best tickets or restaurant reservations, sometimes you need to set reminders for when these opportunities become available. Do you want that 8 pm Saturday night slot at a hot eatery? You need to set a reminder to get online right when reservations for that day are released. Same for some tickets. If you take turns with someone else in the planning, then you need to set reminders for when it's your turn to plan. Also, add your date night plans to a shared calendar.


4. Performance Notes. Figure out what activities you liked and which you didn't. For example, I had season tickets to the opera three years before I admitted to myself that I wasn't the opera-going type. I like places with set menus, but I'm always disappointed with overly expensive places (I’ve never felt like dinners that were more than $160/person were worth it). Keep notes on when and how to get good deals. I keep a record of the restaurants we've gone to and what we should order if we return through Airtable. This is especially useful because we travel a lot, so I remember our favs from Sydney to Beijing.


This approach has led to some pretty fun and memorable date nights. Most have been grand successes. Ok, there was that one time we went to the Kennedy Center to see people dance around like birds. But one miss out of dozens of hits - Ill take those odds!


Do you have any tricks to streamline your date night planning? Shoot me an email and let me know!



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