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Spend Under $100 on Valentine’s Day Dinner at these 5 Highly-Rated D.C. Spots — Dessert Included

January 30, 2020

I’m back! & I’ve got you with a sensible list of restaurants I know you, and your date will love for under $100, dessert included. 

Valentine’s day is expensive. 

How do I know?

U.S. research has shown that in the U.S. alone, there’s a significant spike in breakups between February 1-13th. 

Coincidentally, the number droops back down in March, where thoughts of three-course Valentine’s Day Dinner and long-stemmed red roses are long gone. 

Ahhh, genuine love

But for those of us brave enough to hand over our credit card in for an evening of ultimate showmanship, fret not! 

Underneath the layer of pricey well-appointed, traditional steakhouses and curated, high-grade sushi bars, courting the new lady/man in your life doesn’t have to rob you of hundreds of dollars. 

And it doesn’t have to mean posting up on a dirty sidewalk having Adam’s Morgan Jumbo Slice on a Friday night, muttering disappointment in between bites of congealed cheese and mushy dough.

I’d never do that. 

These are spots that’ll swoon your date before you can and keep your wallet fat. 



Southern Plates + Drinks with Spunk

Penn Ave.’s Barrel is as low-key as it gets without the fuss of pretentious D.C. dining. No valet. No reservations. Get drunk. Call an Uber. 

Mostly about the charismatic drink menu — aluminum beers, whiskey, bourbon cocktails, barrel-aged mixed drinks, you know, the usual– but also about sumptuous, scratch-made plates, that don’t sit on your gut. 

No matter what you or your date order, drinks are less than $15, unless you want to share an entire barrel for $80. 

Oh, and those scrumptious, scratch-made plates like run mostly under $20 in all categories — appetizer, entree, and dessert. 

Featured Entrees

Fried Chicken served with a buttermilk biscuit, red-eye gravy, and apple bacon marmalade 

Tagliatelle Alla Carbonara, panko-crusted egg and half-smoked bacon

Featured Dessert 

Graham Cracker-Crusted Cheesecake

Medium Rare

Bistro, Candle-lit Setting + Steak

My first introduction to Medium Rare back in 2015 was by mistake; Capitol Hill Matchbox’s wait time was too long. 

 I’ve remained in love with the simplicity and straightforward of Medium Rare’s no-brainer fixed three-course menu for $23.95, featuring pate de champagne, a mixed-salad, and their award-winning culotte steak and hand-cut fries.

If your date doesn’t settle for anything less than a steak dinner, resolve your conundrum with Medium Rare. 

Dessert is no problem here either. 

I recommend their Grandma’s Apple Pie, but if you and your date need something a little more gooey, have any of the six desserts for $9 each, including a six-layer carrot cake and a double chocolate fudge three-layer cake

Timber Pizza 

Not Your Average Wood-fired Pie

If you want wood-fired pizza, without where artisan dough-meets cool-kid-neighborhood vibes in a cozy setting, this is it. 

Timber Pizza comes from the same carb-loving duo serving up those crackly, soft breakfast bagels at Call Your Mother Deli on Georgia Ave. 

 Without question, Timber remains my favorite fast-casual, eat-in pizza spot, definitely for the pies, and just as much for the character of the place.  

There’s so much to love; the best spot in the house: the swing chair with a street view is a scene for flirty teenage romance; the uber-nostalgic 90s and 00s playlist will make you sway and sing along to the lyrics or get lost in conversation underneath it all. 

And of course, the wood-fired pizza with premium, locally-sourced ingredients is a thoughtful collection of white-, red -, and green pizzas for a night of uninterrupted enjoyment and praise.

Timber creates an experience similar to that of a restaurant. 

After ordering your pizza, take a ticket; find a seat at any wooden bench indoors or outdoors, or order a drink at the bar; they’ll serve your pies hot on an aluminum tray, with a set of matte white plates. 

Featured Entrees 

 Pretty in Pepperoni – Everything you expect: a pretty sight and plenty of peps

 The Bentley – A sweet, tangy blend of cured chorizo, soppressata, and Peruvian sweet peppers 

Featured Dessert 

Seasonal Ice Cream and Wood-Fired Cone Platter

Unconventional Diner

Easy, Satisfying Unique Dishes, Made Pretty w/ French Techniques

Don’t let the clean plating and fancy techniques fool you; what Unconventional Diner serves is every bit as comforting as having your mother drape a warm blanket over you.

Since my first visit, Unconventional Diner has slowly driven up the ranks as one of my favorite brunch spots. 

The restaurant is chef-driven by an awarded protege of the late Michel Richard, Chef David Deshaies, who worked with the late chef for 17 years. 

As of recent, the diner continues to create buzz around D.C. with it’s a globally-inspired and eccentric dishes, and — as the name states– unconventional direction on diner food that omits the taste of the greasy spoon. 

The menu doesn’t span a few pages like traditional diners but is varied enough to offer you and your date a few choices in each category, most dishes between $7-25

Featured Entrees 

Spring Rolls with “Franch” Dressing 

Carribean Shrimp and Grits featuring Andouille Sausage, Plantains and Pineapple 

Sopa Criolla, a Peruvian Soup featuring Angus Beef, Potato, and Fried Egg

Featured Desserts

Carrot Cake 

Mocha Sundae

Apple Cobbler “A la Mode”

Tiger Fork, D.C.

An Escape to the Streets of Hong Kong

The lady wants Asian cuisine, but not your omnipresent  Eastern’s or Goody’s  Carryout down the street.

In comes Tiger Fork D.C. 

Strut on the playful side — just a little — with playful, reimagined dishes inspired by Hong Kong’s street food scene, existing discreetly in Shaw’s historic Blagden Alley and thumps with energy until 12 AM from Tues-Sat. 

Share and look longingly into your date’s eyes over mouthfuls of fried rice, and for dessert their whimsical, overloaded Bubble Waffle; all except for one dish fall under $25.

This leaves plenty of room in the budget to explore Tiger Fork’s extensive drink menu of wines, cocktails, sake, a Japanese rice wine, beers, and bubbles.

Either way, you’re in for an evening that is an escape to the unusual, and a you-don’t-have-to-go-home-because-you-can-come-here vibe.

Featured Entrees

Frog Legs with Meyer Lemon Puree

Beef Chow Fun with Brisket, Bok Choy and Rice Noodles

Char Siu Plate

Featured Desserts

Bubble Waffle

Egg Tart

Asiah G.

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