Wining, dining and pickup lining
What to do for V-Day whether you're single, on a first date or have been together for so long you pee in front of each other.
Love Hater’s Ball
V-Day haters, the chance to air your grievances is nigh. The ab-ulous Ladies of Fitness spin tunes to the theme “love blows.” Indeed. Cole’s (2338 N Milwaukee Ave, 773-276-5802). Fri 12, 8pm–1am; free.
Little Red Dress Valentine’s Day Party featuring Brody Jenner
Nothing screams Valentine’s Day like squeezing into a teeny red dress, milking free VIP access and clawing bitches for the chance to mount a reality TV star. enclave (220 W Chicago Ave). Sat 13, 9pm; free admission with R.S.V.P. before 11pm; after 11pm and men $20.
Chicago Hauntings’ Guns & Roses Tour
This Valentine’s Day, see the spot where John Dillinger fell to his shu-nuh-nuh-nuh-knees-knees with author and ghost hunter Ursula Bielski. Meet at 600 N Clark St; R.S.V.P. at chicagohauntingstours.com. Sun 14, 3, 6pm; $28.
The Dating Game
The stage at Wabash Tap will be transformed into that wacky game show of yore. Sign up for the chance to meet your match by asking anonymous (and totally ridiculous) questions. Wabash Tap (1233 S Wabash Ave; to play, call 312-360-9488 or e-mail email@example.com). Sat 13 at 8pm; free.
Flosstradamus presents FlosstradPROMus
You provide the nostalgia—turquoise ruffle dress, silk shirt/gold chain combo, vomiting your parents’ liquor in a trashy hotel room—and Chicago’s dance-party gurus will provide the killer mash-ups. Lincoln Hall (2424 N Lincoln Ave, lincolnhallchicago.com). Fri 12 at 10:30pm, $7.
All Is Full of Love Valentine’s Day edition
Strap on your swan dress. DJ Greg Haus presents a Valentine’s Day celebration complete with music, videos, remixes and live footage of Iceland’s violently romantic chanteuse Björk. Berlin Nightclub (954 W Belmont Ave, berlinchicago.com). Fri 12, 9pm–1:30am; free before 11pm, $5 after 11pm.
Bring new meaning to the words speed dating by getting loaded on buy-one-get-one-free lattes while telling your life stories at a hummingbird’s pace. Buzz: Killer Espresso (1644 N Damen Ave, 773-366-8377). Fri 12–Sun 14, 8-ounce latte $3.25.
Erotic fiction contest
Readings of original smut by Chicago authors let you test your new love’s threshold for trash at teeny watering hole the Whistler. The Whistler (2421 N Milwaukee Ave, contact firstname.lastname@example.org to submit a story). Sat 13, 7–9:30pm; free.
Sweetheart sing-along plus a screening of Casablanca
Hide nervous conversation under unabashed awkwardness: Sing “You Are My Sunshine” with a live organ, then watch a screening of celluloid classic Casablanca. Music Box Theatre (3733 N Southport Ave, tickets: musicboxtheatre.com). Sun 14 at 2pm; $11, “Sweetheart Deal” two for $20.
Sweet Saturdays at the Garfield Park Conservatory
Lose the winter blahs by sampling natural treats like the ones that grow inside this lush conservatory. Enjoy live tropical tunes, taste real vanilla and huff scratch-and-sniff cinnamon bark. Garfield Park Conservatory (300 N Central Park Ave, garfieldconservatory.org). Sat 13, 11am–4pm; $3 suggested donation.
An evening of love and betrayal at the Old Town School of Folk Music
Think The Crying Game meets cupid: Old Town School friends and faculty including eerie songsmith Daniel Knox and cello “aggravator” Helen Money pay tribute to the darker side of Valentine’s Day. Old Town School of Folk Music (4544 N Lincoln Ave, tickets: oldtownschool.org, 773-728-6000). Fri 12 at 8pm; $15, members $13.
Private time on Willis Tower’s the Ledge
Romantic dream No. 2712 realized: Willis Tower offers private time on the Ledge, for anything from proposals to renewing vows to screaming “ANTS!” at the folks 1,353 feet below you. Willis Tower (233 S Wacker Dr; call 1-877-759-3325 to book 30-minute or one-hour sessions). $15.95 and up.
Heart Shapes family workshop
If you’ve been married for so long you’re bored (admit it), get entertained by what your kids make at this class. Tots mold a clay heart-shaped gift and then personalize it with stamps and glazes. Let’s just hope it’s not a cancer turning black. Lillstreet Art Center (4401 N Ravenswood Ave, R.S.V.P. at lillstreet.com or 773-769-4226). Sun 14, 2–4pm; $30, members $25.
Valrhona Hot Chocolate
The neurosis associated with new relationships is over. What better way to celebrate comfy love than with a gourmet cup of hot cocoa at a fancy-schmancy hotel? Seasons Lounge and Conservatory at the Four Seasons Hotel (120 E Delaware Pl; 312-280-8800, fourseasons.com). Two servings $15.
A Fine Romance: Jewish Songwriters, American Songs
Author David Lehman discusses his book, which examines early popular love ditties penned by Jewish composers such as Irving Berlin and Rodgers and Hammerstein. And Neil Diamond. Not. Spertus Institute of Jewish Studies (610 S Michigan Ave; tickets: 312-322-1773, spertus.edu). Sun 14 at 2pm; $18, members $10, students $8.
Latin lovers sharing menu at Nacional 27
Holy V-Day deal, Batman! Stick around after dinner for sizzling, Miami-inspired salsa dancing. Gloria Estefan would be proud. Nacional 27 (325 W Huron St; reservations: 312-664-2727, nacional27.net). Sat 13, Sun 14; first seating 5–7:45pm includes three courses for $45; second seating 8–10:30pm includes five courses and a Champagne toast for $75.
Puppy Love 2010
Your spouse knows you love him (we hope). Bring your other faithful companion to Copa Lounge where humans get cheap booze and four-legged creatures receive free treats. Begging not permitted. The Copa Lounge (1637 N Clybourn Ave; 312-642-3449, copalounge.com). Sat 13, 8pm–3am; free.