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What to watch this Valentine’s Day

Darcel Rockett, Nina Metz, Michael Phillips, Tracy Swartz, Hannah Herrera Greenspan and Kevin Williams
Chicago Tribune

From “Love Life” to “True Romance,” we’ve rounded up 11 films and TV shows to stream this weekend for Valentine’s Day.

“Love Life”

“Love Life” is a must-binge this weekend. If you have a mate, and especially if you don’t, these 10 episodes put the search for love in perspective with the quirkiness of Anna Kendrick as Darby Carter. We go along with her as she searches for love throughout her 20s and 30s, often in all the wrong places. You laugh, you cry, you see how your search for love is not unique, which is comforting. But it’s the growth that she makes in her relationship with herself and those who are constant in her life that gives you the warm fuzzies. Perfect escapism for these modern times when dating is a little more tenuous. (HBO Max) — Darcel Rockett

Zoe Chao, left, and Anna Kendrick in HBO Max's "Love Life."

“Love Jones”

Writer-director Theodore Witcher was just 26 and a Columbia College Chicago alum when he made his debut feature about a poet (Larenz Tate) and a photographer (Nia Long) who fall in love. The romance is set against the backdrop of Chicago’s black poetry underground, and Witcher told the Tribune at the time of filming that “all the characters are based on people I knew, or myself. Almost everything that happens in the movie happened to me or friends of mine.” (HBO Max, VOD) — Nina Metz

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“I Know Where I’m Going!”

One of my favorite movie romances, and favorite movies, period, celebrates the role of chance, luck, bad weather, wildly conflicted loyalties and the power of kindness in any love story worth the risk. Filmed near the end of World War II, Michael Powell and Emeric Pressburger’s sublime 1945 black-and-white folktale stars Wendy Hiller as the forthright fiancée of an industrialist (never seen on screen). She’s trying to get to the Scottish Hebrides isle (fictional) of Killoran for her wedding, but on Mull she meets a naval officer on leave (Roger Livesey). A whisper of the supernatural; teenaged Petula Clark in heart-shaped eyeglasses; a spectacular evocation of things just beyond our control — this one has everything. (Amazon Prime, Criterion) — Michael Phillips


Chicago singletons Sloane (Emma Roberts) and Jackson (Luke Bracey) hate the holidays, but devise a plan to endure them together just as friends. “Holidate” follows the pair as they celebrate various special occasions as each other’s plus ones — until romance enters the equation. (Netflix) — Tracy Swartz

“The Lake House”

Chicago Dr. Kate Forster (Sandra Bullock) trades her beautiful glass lake house home for a city apartment. Before she departs, she leaves a letter in the mailbox requesting the new tenant to forward her mail. Meanwhile, Alex Wyler (Keanu Reeves), an architect, buys a lake house and finds Kate’s letter ... from two years in the future. Fighting time and the limits of their patience, the lovers exchange letters via the magical mailbox and try to find a way to finally be together. Chicago cameos include the Green Mill Lounge, the Riverside train station, Miller’s Pub and many trips on the “L.” Alex even takes Kate on an architecture tour through the city, including gorgeous shots of the Tribune Tower and LaSalle Street Bridge. (Amazon Prime, VOD) — Lauren Hill

“While You Were Sleeping”

Although “While You Were Sleeping” takes place over Christmas and New Year’s, this romantic comedy is perfect to watch for Valentine’s Day. CTA fare token collector Lucy Moderatz (Sandra Bullock) has a long-time secret crush on a handsome commuter and complete stranger, Peter Callaghan (Peter Gallagher). After a group of muggers push Peter onto the tracks at the Randolph/Wabash station, Lucy jumps down and saves him from the incoming “L” train. She goes with him to the hospital and learns he has fallen into a coma, but is denied visitation because she’s not family. A nurse overhears Lucy mutter to herself, “I was going to marry him,” and tells the staff she is his fiance, when the rest of Peter’s actual family arrive, craziness ensues. The film features stunning views of Chicago via the “L.” (Disney+, VOD) — Hannah Herrera Greenspan

“Return to Me”

This movie is all about heart. Minnie Driver plays a Chicago waitress who receives a heart transplant from a zoologist who dies in a car crash. The zoologist’s husband, played by David Duchovny, is heartbroken — until he makes a love connection with the waitress. (VOD) — T. Swartz

“About Last Night …”

Adapted from the David Mamet play “Sexual Perversity in Chicago,” this ’80s classic includes distinctive Chicago touches, including 16-inch softball and a romantic stroll along the lakefront path. Demi Moore and Rob Lowe star as 20-somethings grappling with their class differences and what they expect from a serious relationship. (Sling, VOD) — N. Metz

“Never Been Kissed”

Twenty-five-year-old Chicago Sun-Times copy editor Josie Geller (Drew Barrymore) returns to her former high school and poses as a student for an undercover investigative story on teenage trends. Geller enlists the help of her younger and popular brother Rob (David Arquette) to enter the in crowd, meanwhile she falls for her hunky English teacher (Michael Vartan). (Hulu, Amazon Prime, Sling, Starz, VOD) — H. Herrera Greenspan

“Work in Progress”

Starring Chicago improviser Abby McEnany, this semi-autobiographical portrait covers everything from depression, new love, deep-seated insecurities and simply making it through the day. At the show’s core is Abby’s wonderfully self-deprecating lesbian who, much to her surprise, falls for a trans guy (played winningly by fellow Chicago actor Theo Germaine), who falls right back. The show, which was renewed for a second season, is wonderfully knowing, brutal and funny, and it was shot entirely in and around the city. (Showtime, Sling) — N. Metz

“True Romance”

Even the title smacks of Valentine’s, people. This is the story of Clarence (Christian Slater) and Alabama (Patricia Arquette), a couple thrown together by circumstance. This movie has everything, including a hilarious story and scene-stealing cameos from a coterie of actors, including Brad Pitt, Christopher Walken and Dennis Hopper. True love always wins. (Hulu, Amazon Prime, Sling, Starz, VOD) — Kevin Williams