Jared and Jordana begin the week of Valentine’s Day with a conversation about how to celebrate the holiday in 2021. A listener writes in to ask whether or not she should expect the guy she’s only been dating for 2 months to plan something this year. J&J rate the level of V-Day expectations at every stage of a relationship, explaining exactly how much effort is required based on the milestones you’ve hit. The Awkward Sexual Encounter involves period sex, a flung condom, and a lot of cleanup. Then another listener asks why the guy she just started dating asked her to go on vacation together, then backed out at the last minute. Is he showing that he’s unreliable or just trying to avoid getting too serious too soon? They read a text message exchange about the cancelled vacation and tell us what’s really going on here. Finally, this week’s Red Flag or Deal Breakers feature a debate about whether or not you’re required to split lottery scratcher winnings with the person you’re dating.