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After Kevin and Vanessa witness Kyle's success using a dating app that requires a close friend to choose one's perfect match, they agree to be each other's wingman and try their hand at matchmaking.
When Vanessa is featured in a local magazine article about entrepreneurs under 40 years old, a jealous Kevin tries to get attention for himself by securing his own award, while reminding her that she is over 40. Also, Chale fixes up Kyle on a date with his wild Aunt Kristin.
After convincing Kevin to break things off with his neighbor, Wendy, who had reeled him in with her delicious meals, Vanessa feels compelled to cook for him despite being culinarily challenged.