5 dates in, and I’m thinking about Valentine’s Day. What should I do?

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throwaway88008 asks:

So I’m about 5 dates in, and thinking ahead to V-Day.What’s my move? Late 30s hopefully couple to be.

Should I just get a reservation at a fancy place? What’s good for wintry plans? I am going to figure out if there’s something specific to our interests going on, but maybe you have ideas I haven’t thought of, and I’m not above pilfering an idea to make somebody else happier.


Demetrius says:

Ah, Valentine’s Day, my least favorite of holidays! I’ve always been against all forms of contrived romance, but I’m not dumb enough to think that my opinion alone on this will sway you. I’m also against the “Anti-Valentine’s” event, because you know, the whole indifference thing eschews caring enough about being against something than to do an event in direct response to it.

ANYWAY, 5 dates in, thinking ahead to Valentine’s Day and now you’re at a crossroads. Just to be clear, it sounds like you want to approach this crossroad more than you feel like you have to. I think that a lot of people feel this vast amount of pressure when they’re dating someone new and Valentine’s Day is approaching that they use V-Day as a marker for how their relationship is going to proceed. If you feel like you want to do that, cool, but don’t feel unnecessarily pressured. It’s just another day, beloved. If you’re someone reading this thinking “Eh, too early to tell” don’t feel like you have to do a big Valentine’s Day thing or that you have to make a huge romantic spectacle out of the day. That said, you’re asking about what you should do, so I’ll tell you.

A reservation at a fancy place is always a great go-to, provided you have the funds to do that. I’ve done it before, and it’s a great way to say “hey, I planned something nice for us” with minimal actual planning. All you have to do is have the money to pay for the date, which is usually a set amount because odds are good that the menu is prix-fixe, and make a reservation (shoutout to Opentable for making me look like I put in tons of effort since 2007). Making a reservation for Valentine’s Day is simple and easy, and since it’s considered a romantic gesture, it’s probably going to be received well if she has fairly traditional or common ideas around romance and Valentine’s Day. It’s a safe bet.

As for Wintry plans, eh, I’d avoid them as a centerpiece of the date. Sure, winter dates are fun, I’ve written about them before, especially about the ones with fireplaces, but they’re more of a fun diversion or change of pace from the norm than anything else. If you make a reservation at a restaurant with a fireplace that’s a solid move of course. If your V-Day date includes fun winter activities like ice-skating, cool, but I wouldn’t make it the focus of the date. You either go full romance or not, no middle ground. Don’t take your Valentine’s Day date out to make snowmen and not do something romantic for them.

With that said, a fancy reservation isn’t your only option. A date is only as romantic as the intent and activities, not only the setting you’re in. Here’s a twist on the formula: You don’t have to do a big fancy dinner. You didn’t get into your specific interests, but here are some ideas that might work for just about anyone:

  • Sporting event if you’re both into sports
  • Go see a show/band you both like
  • Go to a Comedy show
  • Go see a movie you’ve both been dying to check out
  • Plan a night in

Of this list, I’ve done a few of these activities on Valentine’s Day, and the feedback I got was positive overall. I’ve also done the classic reservation at a fancy restaurant a few times, feedback being equally as good. I had a good time doing all of these things,but putting down $200 for a dinner that would normally cost $50 isn’t for everyone. You should try to make the night special, no matter what you do, but how you do that is up to you. A card is always appreciated as long as you actually write something in said card. Most people appreciate flowers, and red roses are the quintessential flower for V-Day, but feel free to check to see if the person you’re buying them for actually wants them. You don’t necessarily have to buy roses if you can’t afford them, or you can buy them the day before and put them in water to save a few bucks. They’ll keep, trust me on this. You can always buy a single red rose, and if they’re solid people they’ll appreciate it.  Chocolates and sweets are pretty much a standard gift, and you don’t have to blow your budget here. If the only thing you can afford is discount candy, just don’t buy candy. It ain’t worth it, trust me. Last year I wrote a Last Minute Valentine’s Day Guide that you can use as a reference but basically, you don’t have to blow your budget if the romantic intent is there.

Seriously though, the safe bet is the reservation, the riskier but still good bet is the alternate plan that is a bit less staid. You can also be smart about it and do your Valentine’s Date the day before since 2/14/16 is on a Sunday and you can use that as a reason to do the whole dinner thing the day before and save a bunch of money. You’re welcome.

Good Luck Out There.

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