In “Both Sides of a Breakup,” the Cut talks to exes about how they got together and why they split up. Hannah, 32, and Brian, 34, were crazy about each other — until he admitted he was scared to have sex with her.
Hannah: I was single and just turned 30. I was also newly healed and recovered from a breakup with my ex that devastated me. Long story short: I had to leave him, even though I loved him more than anything, because he had a drinking problem. It had been a few months since ending it. The good news was that I was doing a lot of therapy and was in really good shape physically (from exercising all my stress away), and I felt ready to meet someone great and start a healthy new relationship.
Brian: It was Halloween. My friends and I bought tickets to a cheesy party on the Lower East Side because we wanted to meet girls. We didn’t say that in so many words, but we all knew the score. I was dressed like a Yankees player because that’s all I had to work with. I saw Hannah sitting at a table with her friends, and she was dressed like a slutty bunny.
Hannah: I was a Playboy Bunny. I was like, Fuck it. This is the only time in my life my body will be this banging. I’m going ALL-in. Brian and his friends were looking at us and acting really immature — like, giggling and pushing each other toward our table.
Brian: Hannah and her friend were kind of staring at me. I was literally like, “Did we go to college with them? Why do they keep looking here?” I didn’t mind it. Hannah is beautiful. And her boobs were, like, bouncing out of her top. I’m sorry — I don’t mean to sound misogynistic! But … you couldn’t not look.
Hannah: Finally I walked over and said, “If you’re going to stare at us like fucking stalkers, you at least owe us some drinks. We’ll have two margaritas.” Anyway, we all ended up hanging out. I liked Brian the most of all his friends because, well, he was the hottest. But also, he said he worked in a research lab, and my parents are both chemists. I’m a fashion photographer, totally other side of the brain, but I liked that he was in the field. It made me interested in him. I liked his dark eyes and bushy hair and his height, too. I also liked his hands. They were big. Very big.
Brian: It was kind of amazing talking about my job with a girl who could understand it. Most people hear scientist and think I’m, like, a wizard or a super-nerd. And, sure, I’m both! But I’m cool and sexy, too! Hannah saw my multidimensionality.
Hannah: We exchanged numbers, and I felt excited about meeting him. I knew we’d start dating. There was just one dark cloud looming over my head, though: I knew I’d have to tell him about my STD. I have genital herpes. I’ve had it for so long and it’s totally under control, but some guys run when they hear about it. I’ve tried not to let it ruin my life. One in three people have herpes! Basically every celebrity we all worship and adore has herpes! I actually got it from a celebrity (a famous actor I photographed for a fashion magazine in my early 20s). My ex happened to have it, too, which was a huge relief. I’ve dated guys who can’t handle it and guys who give zero fucks — you just don’t know. Brian hadn’t even texted or called yet, but I was dreading telling him. I had a gut feeling he’d be very rigid about it; the scientist’s brain does not leave a lot of room for nuance.
Brian: I texted her the next day. I was really stoked. I hadn’t been in a serious relationship for a while, and maybe I’d had a little casual sex, but it wasn’t really my thing. I’m a worrier, and I struggle with a little bit of anxiety, and it’s hard to sleep around when you have that disposition. So I invite Hannah to dinner and suggest a cozy Italian place in the West Village.
Hannah: He suggested the most generic first-date restaurant spot. But they do have good wine — I’d been on, like, two other first dates there before, so I knew that! I was excited and also filled with dread. I always tell guys on the first date about the big H. I have no interest in wasting my time with someone who’s going to be a hater.
Brian: The date was awesome! She was so beautiful and so smart. I loved hearing about her work. I felt the chemistry for sure.
Hannah: I couldn’t relax on the date until I told him. But I needed, like, two glasses of wine first. I felt like throwing up because I was so nervous. I liked him so much already! Finally I was like, “I need you to know something. About eight years ago, I had unprotected sex and got an STD. I take Valtrex every day and haven’t had a flare-up since the first one. The risk of transmission is extremely low (especially if we use protection). It’s honestly not an issue, and I’d be happy to never talk about it again — or talk about it with a professional together — but I am always up front about it. Are you comfortable with any of this?”
Brian: It took me a minute to process what she was saying. She was so self-aware and elegant about it. But truthfully, I’d never had a conversation like that in my life. Not even close. I remember just sipping my beer and trying to not sound like an insensitive man, or an asshole, about anything. But seriously — I had no idea what to say or do next.
Hannah: Spoiler alert: The rest of the date was a little bit weird.
Brian: I was just like, to myself, I’ll get back to this tomorrow. I wanted to have fun that night.
Hannah: We did kiss that night. And, of course, it was amazing. I was so attracted to him. His kissing was everything. I went home panicking that he’d ghost me after the information I gave him, though. It was so nerve-racking. I felt sick for the next few days. But he was definitely texting me and giving me a lot of reasons to be hopeful and calm the fuck down.
Brian: You know how guys are; we don’t know how to talk about things. I couldn’t ask my friends what to do because I liked Hannah and didn’t want anyone to judge her. I remember being scared to even, like, Google herpes — because it made me paranoid people would think I was a carrier. I ended up talking to my older sister about it. She was like, “It’s fine! Get over it!” So I tried to.
Hannah: I was so relieved when he hit me up for the second date. I think that one was a concert in Central Park. Again, it was great. He was so sweet. We held hands. By our second date, we honestly felt like a couple.
Brian: We started seeing each other quite a bit. She was the perfect fit for me. We had so many similar interests — in music, in travel. We both wanted to visit Costa Rica and would text each other flight deals and cool-looking hotels. It just escalated really fast. Like, every other night, we were hanging out. She made me really happy.
Hannah: Fuck, it was so stressful. We would have these epic dates and then make out at someone’s apartment and maybe, like, touch each other over our clothes. I would rub his dick over his jeans but never unzip them. It was just strange. We are grown adults, and I’m a sexual person! But I was just taking his cues, and he was moving really slow. I was super-horny for him. But he would never do more than feel me up or maybe put his hand over my underwear for a few seconds. My mind was torturing me. Like, was he teasing me and being sensual, or was he literally afraid of my pussy?
And let me say here I love my pussy. I’m not mad at her. We all have un-fun health and dermatological issues, and this is one of mine. It’s okay! Ya know?
Brian: We dated for two months. For the third month, I had to work overseas and we were texting and FaceTiming all the time. We hadn’t had the “Are you my girlfriend?” conversation, but she was pretty much my girlfriend.
Was I afraid to have sex with her? No. I mean, not really. It was just, like, this subconscious thing, I think. Like, intellectually, I was okay with her STI. I understand how medicine works; I’m a scientist. I could research it and make sense of it. And she’s right: It’s really not a big deal. But deep beneath the surface, in an ugly place I’m ashamed of, I think I was fearful. I was avoiding sex, even though none of that was Hannah’s fault. She’s as sexy and attractive as anyone I’ve ever dated — or probably ever will.
Hannah: When he came home, I had written a script that I had practiced and was ready to say to him. I couldn’t take it anymore — feeling dirty or undesirable. I couldn’t handle the unspoken sexual tension and weirdness. So I said, “We need to talk about sex. Are you craving it as much as I am? Do you think it’s time we cross that path? Do you want to figure out how to do it in the healthiest possible way? We have lots of good options!”
Brian: I remember meeting up after I got home. It was a bar, and it was kind of hard to hear. I was also really jet-lagged. And I just was not evolved enough for the conversation. I was like, “Yeah, I can’t do it. I’m sorry.”
Hannah: The entire date lasted about 20 minutes. He was like, “I’m too scared.” And I was like, “I wish you all the best, but good-bye.”
Brian: I hated myself for how I handled the conversation. I knew I was a better man than that. The truth is I hadn’t really thought about why I wasn’t having sex with her. I knew I was scared, but I kept putting it off and blowing the whole thing off mentally. I just didn’t know what to say or what was going on with me. There was no part of me that felt relieved it was over. Hannah was the best …
Hannah: It was a stab in the heart, but I was happy to be done with someone who wouldn’t accept me for who I was. That’s a terrible, terrible feeling. No one deserves that. I’m glad our relationship was short. I really like Brian, and we are friends now. We get lunch sometimes, and we laugh about our little romance gone wrong. I think he’d probably be happy to rekindle, but I put a wall up, as far as that’s concerned. It was hurtful … very hurtful. I’d never date him again.
Brian: I was an idiot. No one I’ve dated even comes close to Hannah’s intelligence and compassion. She’s so articulate and classy and beautiful. I’m ashamed of how I acted. Would I do it differently now? One-hundred percent! But she’d never give me that chance. I’ve asked, and she’s told me.
Hannah: I’m mostly dating on Feeld now. I’m not into kink, really, but it’s so much easier to disclose STDs on there. No one cares. I mean, they care, but it’s like, “Cool, we’ll figure it out! Thanks for telling me. Transparency is so fucking sexy.”
Brian: I’m super-single. Been a real dry spell since Hannah, which ended, like, a year ago. But, yeah, I guess that’s my punishment.