Dating Was So Hard, Until It Wasn't from Death, Sex, & Money

"When I want it badly enough, I can...really steel myself and just be like, 'Don't freak out, just stay still, kiss them. Just do it!'"  This is how Katie Heaney talked about her dating life when we first spoke back in 2014. She'd just published her confessional first book, Never Have I Ever: My Life (So Far) Without a Date—a chronicling of her lifelong singledom until age 25. And she'd recently moved to New York City from Minnesota to take a job at BuzzFeed as an editor. When we talked, the 27-year-old was also a virgin—something that made her really uncomfortable. "I really don't like it," she told me. "And I also hate that I don’t like it. Because that feels like conceding that it bothers me and that I am susceptible to the opinions of others."  Listening back to herself two years later, Katie winced. "I hear myself talk about all the fear and the dread and 'making myself,' and I'm just like, 'Ugh, you don't have to feel that way,'" she told me. Now 29, Katie says she's adjusted to life in New York—and along with that adjustment, has also come to terms with the fact that she's gay. "I remember being on the subway and looking around at all the guys. And being like, 'I don't want to date any of you. Like, I just don't - I don't want this,'" she said. "And...the attraction like fell out of my body." Soon after, Katie started dating a woman, and says that while she was nervous on their first date, she wasn't "uncomfortable to [her] core" in a way that she had been in the past on dates with men. Despite her newfound comfort in her sexuality, Katie says she's still learning how to be in a relationship. "I have to learn how to not catastrophize every disagreement or every feeling that comes to me that isn't a 100 percent joyous one," she told me. "I thought that I had struggled so long to find [a relationship] that once I did, it would just be perfect or easy. And, you know, I was naive about what it really means to spend that much time with someone."  If you like what you heard, subscribe to DEATH, SEX & MONEY for free.