Sidebar: He's Hooked Up With All His Friends

Meredith and producer Katelyn Harrop take on two new letters, including one from a woman in her 40s who digs her new boyfriend but wasn't thrilled to learn that he'd previously hooked up with most of the women in his friend group. Is this a red flag, or just ancient history? Email your dating and relationship questions to loveletters@boston.com. Learn more about your ad choices. Visit megaphone.fm/adchoices