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Walden, depressed about being single on Valentine's Day, tries to convince Kate to give him another chance. Meanwhile, Alan's Valentine's Day plans take a turn for the worse.
Alan has concerns when Jake brings his 36-year-old girlfriend home for a visit. Meanwhile, Walden tries to keep a secret from Alan.
When Walden runs into his ex-wife at a high-end singles mixer and they talk about getting back together, Alan worries that she's not good for Walden.