10 Creative Valentine's Dates - 2/10/10
(without breaking your bank account*)

*Because otherwise I would just say get a limo to the airport, and fly her to Paris to have dinner at the top of the Eiffel Tower, which you've had dipped in gold.

So it's Valentine's Day. The day the girl you're dating is expecting something more than the "ordering Dominoes and watching 30 Rock" that's usually enough to get you some passable nooky.

That's right, the day YOU have to be (gasp) creative, lest you want to spend the last part of the night alone in her bathroom, working off to a partially downloaded picture of Jessica Alba on your Blackberry, or worse yet, buy her jewelry to make for being a total suck boyfriend who can't even come up with a good Valentine's date.


Luckily, other people have already been creative, precisely so you don't have to. You just have to keep her from reading this website.

1. The "Choose Your Own Adventure" Date

COST: $50-$120, depending on the restaurants/activities
GOOD FOR: All types of girls, even those you haven't been dating very long.
LIKELIHOOD OF BONAGE: Very High

THE DATE: Remember those books when you were a kid? Yeah, kinda like that, except your date won't end up getting her brain devoured by leprous gnome-aliens from the planet Groton (hopefully).
Don't tell your date anything about the date (except what to wear). Show up at her house and tell her you're going to be having a "Choose Your Own Adventure" Date, and that the events of the date will depend on her selections. Then give her cryptic choices like "North or South?" that link with the activities behind them: If she picks North, do something you would do in the north, like ice skating. If she picks South, do something you would do in the south, like horseback riding. Or starting a drug cartel.
After the first activity, give her another choice, like "East or West?", that combines with the prior choice for dinner, like North + West: Surf 'n Surf, or South + East: Cajun BBQ

CAVEATS: It can get a little complicated if you have more than two steps (not to mention you have to plan 4, 8 or 256 possible date permutations) but trust me, it will have worked by this point. After the main events are over, feel free to end the night with some choices of your own: Wine or Champagne? Your place or hers? Traditional or rodeo-style?

2. The Astronomy Lesson

COST: Free
GOOD FOR: Nerds, night-owls, and girls who think it matters what your sign is.
LIKELIHOOD OF BONAGE: Very High

THE DATE: Take your date to a mountain campsite or a romantic nature preserve or unobstructed roof deck and embark on a night of storytelling and lying side by side as you show her all the constellations and explain the fascinating mythologies behind each of them. This can last for an hour or all night, depending on how much Greek crap you can cram in your noggin. Note: you do not actually need to be naturally knowledgeable about stars or myths for this - there are any number of websites where you can learn everything you need to know. Just do it at work, when you'd normally be surfing Stumbleupon. You can also just make stuff up - your date's probably not going to know that the Reverse Cowgirl isn't an actual constellation.

CAVEATS: You're f*cked if it's cloudy - better have a backup plan, like your local planetarium. Bad news: Planetarium ushers usually don't like you telling your own stories during their show, and/or trying to slip your date the old two-finger salute. Good news: If you do succeed in this, you've got a hell of story for the grandkids.

3. The Five-Star Shitty Restaurant

COST: $5.99 (unless you choose steak, then $6.49)
GOOD FOR: Girls with a senses of humor and/or terrible eating habits.
LIKELIHOOD OF BONAGE: High (or very low, depending on the girl)

THE DATE: This one's all in the set up. Don't tell her where you're going, just tell her to dress up super nice, show up in Tux or suit, with flowers, borrow a friend's car that's much nicer than yours, drive her to the most expensive restaurant area in town… and then go to Taco Bell.
Sometimes that's enough. But you can keep going. Bring in your own silverware. Drink Sierra Mist out of wine glasses. Mild Sauce out of tea saucers. I've found most Taco Bell managers will let you put a table cloth on their tables, as long as you talk to them first, and don't keep referring to it El Table Cloth Supreme.

CAVEATS: Super high-maintenance ladies generally don't see the humor/cleverness in this idea, so if you're dating one… well, dump her and start dating a cooler chick. This date also works phenomenally with homeless women.

4. The Picnic Hike

COST: $30
GOOD FOR: Out-doorsy types; girls you're planning to murder/bury at the end of the date.
LIKELIHOOD OF BONAGE: High

THE DATE: As much as we humans try to make our museums, opera houses and Vegas Casino lobbies beautiful, there's just no competing with nature. Find the most pristine beach, gorgeous park, or scenic mountain top wherever you live, drive your date 95% of the way there, (because no girl wants to walk 10 miles on Valentine's Day) then hike it. Don't tell where you're going, just to bring good walking shoes, and have a picnic waiting for you both at the end, all set up. This means you'll have to make the hike twice yourself, but that's a small price to pay for cheeks.

CAVEATS: This IS the great outdoors, so there's always the risk of a potentially sweaty or tired girlfriend, or a cougar attack. And we don't mean having your Valentine's date turn into a threesome with a feral, 40-year-old MILF.

5. The Cheesiest Date Ever

COST: $80-$150, depending on the thickness of the cheese
GOOD FOR: Girls who hate Valentine's Day and syrupy romance stuff. Also, girls who LOVE Valentine's Day and syrupy romance stuff.
LIKELIHOOD OF BONAGE: Fair

THE DATE: For the Post-Modern, Smuggly-Self-Referential date on this list, I recommend the Cheesiest Date Ever. Instead of avoiding the usual Valentine's Day clichés, do ALL of them. The heart-shaped box of candies. The rose petals leading down her steps. The Hallmark card with the stuffed animal. Take a long walk on the beach. Go to a candle-lit Italian restaurant and meet in the middle of a strand of spaghetti. Go to an ice-cream shop and share a milkshake with two straws. But you have to do it all to get the effect. You can set it up at the beginning by telling her you're taking her on the most original date ever, or just let her get it as you go along. Assuming she hasn't ditched you after the stuffed animal.

CAVEATS: Just don't make the same mistake I did and do this for your first Valentine's Day with your lady, lest you spend the rest of the decade proving that you actually are creative because she didn't get the joke.

6. The Treasure Hunt Date

COST: $30 (and a bunch of set-up time)
GOOD FOR: Better for girls you've been dating for at least a few months, so they don't think you're going to kidnap/rape them. Also good for pirate girls.
LIKELIHOOD OF BONAGE: Very High

THE DATE: Picture this: your date answers her door for your Valentine's Date to find only a note. A short poem; a clue, leading her to her next hint, with the promise of a wonderful reward at the end. The clues lead her around to different places of meaning to the two of you, and finally end in a garden somewhere where you're waiting with flowers. And a picnic (yes, again with the picnic thing, but picnics are underratedly romantic). And perhaps a more complete poem, painting how much you love her, now that the theme's been set up. If you do it right, she might just jump your bones right there.

CAVEATS: OK, a few for this one. One, as with many neighborhood dates, this works much better in some areas than other. College campus: great. South Central: not so much. Two, it's essential to find a good way to reassure your girl that you'll be close by as she's wandering around, keeping her safe… without making yourself sound like a crazy stalker. And finally, do not write poems if you are a shitty writer. You can write regular riddle clues if you're more comfortable with that, or draw pictures. Or just cut up a Google map.

7. The Double Massage

COST: $40-$80
GOOD FOR: Nymphos, or any girl who likes a nice massage. Not good for girls who already work in massage parlors.
LIKELIHOOD OF BONAGE: High

THE DATE: This is perhaps more a gift idea coupled with an end-of-the-date idea, so you might want to throw a dinner in there too, or at least an Acapella Show or something… But anyway, the idea is you give her two massage gift certificates, one for a professional place with words like "Serenity" or "Xanadu" or anything French in the title, and the other for an amateur massage, from you. And not just your usual "I'll rub your back from two minutes in the hopes of getting a blowjob" massage - actually buy oils and crap. This way, you've got both your "I'm personal and thoughtful and want to spend time on you" and your "but don't worry I also have money so your girlfriends will be jealous" cards covered.

CAVEATS: Like I said, this is almost more of a gift idea than a date idea, though one of these massages could certainly happen on Valentine's Day (what better V Day could you hope for than ending it with hot oils, or with your girl in a spa while you watch football next door at Best Buy?). I strongly suggest not letting her do both massages on the same day, though (or even near each other), Yours is just going to look shitty.

8. Cook For Her

COST: $30-$60 (get some decent wine)
GOOD FOR: Health nuts; girls too obese to leave the house.
LIKELIHOOD OF BONAGE: High

THE DATE: Find a way into your date's apartment when she gets home from a long day at the office (or Pilates class, if you're carrying all the weight in the relationship). Use candles, lighting, Kenny G, etc to make the place look fantastic, and different than she's used to. Make multiple courses. Make a fire. Drink wine in front of it after the meal, or make s'mores if you're dating a heavy. Play your cards right and you won't have to leave the house (or spend another dime) until morning.

CAVEATS: Do not, at any point in the night, utter the words "So I figured since I did all the cooking, you'll handle the dishes." The words "I figured one of us should do some cooking for once," should also be avoided.

9. Gondola/Carriage Ride

COST: $100ish
GOOD FOR: Most girls, excluding Hydrophobics or equinophobics.
LIKELIHOOD OF BONAGE: High

THE DATE: And not just in New York and Venice, Italy - you'd be surprised, many decent-sized cities have things along these lines - just search online. Carriage rides make ideal romantic transport between one part of your date and another, or take an extended ride and make it the whole thing. Gondola rides can even add dinner (it's hard to dine on a carriage, unfortunately, given the bumps and horses' asses three feet away.) Both are pretty damn sexy and new to most girls.
If your city is too small for these services, a second option would be to construct your own… you know, if you happen to be a boatsmith, or own several horses. Third option is to hire one of those bike carriage guys, though this is a lot less romantic. Fourth option is to hire a hobo to push the two of you around in a wheelbarrow.

CAVEATS: If you actually live in Venice, don't do a gondola ride, because there it's the equivalent to taking your girl on a date where you ride around in a taxi. Same goes for the carriage ride, if you're Amish.

10. Dominoes and 30-Rock

COST: $19.95 (includes cheesy bread)
GOOD FOR: The tenth time you've used this list.
LIKELIHOOD OF BONAGE: Fair

THE DATE: And hey, there's something to be said for "if it ain't broke, don't fix it." Sometimes the best date is just to look your date straight in the eye and tell her you love her, no matter what you do together. Even if it's the same old shit you do every night. Except don't actually say that last part.

And don't say we didn't warn you if you end up at Zales the next day, trying to make up for your unoriginality.

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