Making plans for Valentine’s Day can be VERY stressful. Relax. Take a deep breath (or two), and decide which category your date fits into and plan accordingly.

You can win if you don’t pay. 
Second Saturdays at the Wadsworth
Baby Grand Jazz at Hartford Public Library
Chicago Style Steppin’ Dance Class at Hartford Public Library

Mo money, mo romance.
Bernie Williams Collective at Infinity Hall
Kronos Quartet at the Bushnell
Dinner at ON20, or Max, or Firebox, or your favorite date restaurant.

Does she like me? Will he call? Maybe it’s time for some questions you can actually answer.
Geeks Who Drink Pub Quiz at Hanging Hills
What Trivia at Arch Street Tavern
Tuesday Trivia at the Half Door

For those of you that are totally in like.
First & Last, then Mozzicato’s
Casablanca at Cinestudio
Valentine’s Mixology Class

Two ways to lose your lover.
National Ninja League World Championships
Connecticut Kids Fair

For the love of the lover of the game.
See a UConn Men’s Basketball game
See a UConn Women’s Basketball Game
Get pucky with UConn Hockey or the Hartford Wolf Pack
Watch some pros who can really handle their balls.
Watch this. Proceed directly to second base.

Listen to some sweet sounds with your audiophile.
Latin Lovers at The Bushnell
Jazz Mondays at Black-eyed Sally’s
Off The Record Indie Night

For your funny Valentine
Sea Tea Improv Comedy Night
Brew HaHa Comedy Club at City Steam
Guess what?

Dates that make you go hmm…
A Night of Surrealist Games
The Mouth-Off With Chion Wolf at the Mark Twain House
(See also: Beer Mine)

Your first date started at last call. 
Call a cab, go to the Spigot. Order the drinks you love. Repeat.
Put on a onesie. Go to the Onesie Bar Crawl
Valentine’s Mixology Class

Before there was Tinder, there were other things. 
Vintage Valentine Tea at the Isham Terry House
Behind the Scenes: Love & Lust at CHS