It’s February, which means we can all complain about it officially being the coldest month of the year. To start things off, Jordana tells Jared about her sister’s recent stay at her place and the creative new ways her seven-year-old nephew stress tested her new furniture. Jared’s hot off of a star-studded show at the Comedy Cellar, where Madonna inexplicably performed a 40-minute comedy set. Later we dive into our mailbox, and hear from a listener who worries that all her longterm relationships will end up with a dead bedroom. Also, a recent divorcee finds herself stumbling through her reentry into the dating world and regrettably commissions a pet portrait for a man she was casually seeing whose dog died. In “Awkward Encounter,” Jared & Jordana advise a listener who just realized she went on dates with two guys who are close friends and debates whether or not she should tell them. In “Red Flag or Deal Breaker?“, we hear about a guy who pretends he went to an Ivy League school, an ex-boyfriend who might be a little too obsessed with his sister and a woman who won’t stop comparing the man she’s seeing to her ex. Have a dating question for Jordana and Jared? Send an email or voice memo to [email protected] or leave us a voicemail at our dating hotline 212-589-8903.  Learn more about your ad choices. Visit megaphone.fm/adchoices