News & Politics

Dating Diaries Update: Breaking Up is Hard to Do

Each week, we check in with our Dating Diarists to see what’s happening in their lives when it comes to chemistry, romance, and maybe even love.

Meet our datersDana Neill | Sally Colson Cline | Michael Amesquita | Kate Searby | Max Schwartz | Lucas Wall | Jenn Heilman    

Editor’s note: In an effort to protect the privacy of our diarists’ dates, our updates are on a slight time delay.

Neil Sedaka isn’t the only one crooning about how breaking up is hard to do. Some of our daters are singing the breakup blues as well.

As a Christmas present, Dana Neil gave Florida Guy concert tickets for New Year’s Eve. She was at his house, and unfortunately, the whole thing didn’t go well. “He said, ‘I’d love to see these guys with you, but I already have plans,’ ” she says. “I said, ‘Well, give ’em back,’ and told him I owed him another present. It was kind of awkward. We’ve never discussed a relationship and we’re not serious, but we’ve been seeing each other for three months. We didn’t talk about exclusivity, but we had gotten to the point where we were doing something every weekend. Maybe someone new and shiny came along.”

Before Dana could think about it, Florida Guy started turning off the lights and then asked if she was staying. “I stayed, but the next morning it was weird,” says Dana. “The whole thing was a little bit uncomfortable. He called the next day but didn’t leave a message. I didn’t call him back, and then I got caught up with the holidays. We haven’t talked since. Then recently, I got an e-mail from him. If there was something there or true feelings, then I think he would’ve called. Or I would’ve called. I think it’s time to say, ‘Thanks for the good times’ and move on.”

Dana’s post on Craigslist about how the economy affects relationships sparked some great e-mail conversations, and she’s going to have lunch with one of the men she met through that.

The person Sally Colson Cline had been seeing keeps calling, but she’s not sure she wants to entertain that possibility again. As for meeting someone new? “I have a lot of straight friends, so I don’t go to the gay clubs a lot,” she says. “I don’t want to wear them out with the whole gay-club scene. But one of my straight friends wants to ‘do something gay’ with me so we’ll see.”

“I haven’t been able to find my group of gay girlfriends,” says Sally. “I’m very feminine-looking, and a lot of women look gay. Like me, a lot of girls are attracted to more butch women. I think I’m not attractive to most lesbians. I’ve spent my whole life out of the closet having to be very vocally out. It’s good and bad. I don’t get a lot of the stereotyping that a lot of lesbians get, but it’s difficult to meet people. I always have to come out, whether or not they’re gay or straight. Even talking to guys is weird—I don’t want to jump right out with ‘I’m a lesbian’ because I don’t want to assume they’re hitting on me. But I also don’t want to lead them on.”

Shortly after they made their relationship official, Lucas Wall’s new boyfriend, Justin, went on a family vacation. The two didn’t see each other for a few weeks, though they did talk and e-mail. One conversation raised a red flag for Lucas: “Justin expressed concerns about the long-term viability of this relationship. He touched on some specific things like that he wants to have children, and he got the impression that I don’t. He wants to live in a leafy neighborhood in a single-family home, and I like the city. This came out of the blue. It was a lot to bring up when we’ve been dating for less than three months.”

When Justin got back, the two went on several dates and spent much of the weekend together. “We decided that we wanted to spend some time together without having that conversation right away,” says Lucas. But at the end of the weekend, Justin came over and said things weren’t working for him. “He said the time we spent during the week confirmed his feelings that it wasn’t going to work. He didn’t elaborate, and I didn’t feel like I ever got a real understanding of what’s going on. It was three weeks between when we got together officially and when we first had this conversation. It seemed like a whirlwind. It’s been very difficult for me. I’ve never been dumped before. And adding to that is the mystery of what really happened or changed in that short amount of time. I didn’t have the sense that Justin was the perfect man, but I have come to accept that there’s no such thing. There were things about his personality that weren’t ideal for me, but they were things I could’ve lived with. I thought there was long-term potential. I knew we’d have to address those long-term issues such as kids, but it seemed too soon to worry about that for me.”

Kate Searby has gone out with the producer she mat at Tryst a few more times. “He’s so kind,” she says. “He’s got soul. I’m really inspired by him. He’s a lot of fun to hang out with.” She’s chatted with California Guy on the phone as well. “I like him, but I like [the other guy] a lot more. I don’t have to choose since it’s so early, but I haven’t made the time to see him again.”



Choir Girl took Michael Amesquita to the airport. He asked her what she thought about his changing his Facebook status to ‘in a relationship.’ She said she wanted to play it by ear a bit more. “It’s all right,” he says. “I was looking for more of a definition, but I’m okay with it for now. I’m enjoying where we’re at now. I don’t feel like I want to pursue anyone else, but until it’s more formal I don’t know. And that’s more on her end than anything else.”


After not seeing each other for a while, Jenn Heilman had another date with a man she met on “He came over for dinner, and we watched a movie,” she says. “I like him, but I’m having a hard time getting a good read on him. We always have good conversation, and we have a lot of things in common. Even though he’s very outgoing in the talkative sense, he isn’t in the physical sense. He’s kissed me, but there’s not any cuddling or handholding. Considering he stayed and watched a movie, it’s just hard to tell. I guess we’ll see what happens this week. I think the ball is in his court. Last time I was in this situation, I was accused by a guy of being too aggressive. I have a hard time figuring out what’s too strong. It’s different for different people.”

Max Schwartz had some changes at work that has kept him preoccupied and not focused on dating.