News & Politics

Dating Diaries: The Wrap-Up

For the last few months, our Dating Diarists spilled about their dates, romances, and breakups. As we end the series, they dish on the good, the bad, and the ugly of dating so publicly.

Right before Sally Colson Cline applied for Dating Diaries, she’d been out on several dates. She thought that momentum was going to continue, but it petered out. And, while participating gave her “a little anxiety because I never had anything to report,” she did realize she was in a different place and that sometimes it’s okay to take a break. “After the breakup, I thought I’d feel like a huge player and have a revolving door of women,” says Sally. “What I found out is that I really wanted to reconnect with my friends who were sidelined by my relationship. There are things that are more important to me right now. I don’t worry about my future. I’ve been lucky in love. I’ve dated some amazing women. So I don’t worry about it.” 


Max Schwartz realized that people like to stare into other people’s dating worlds but don’t necessarily want a realistic look at their own. “I thought this whole concept would be a refreshing dose of honesty that everyone would get behind,” he says. “That’s not true. People would like to pretend that people aren’t analyzing each other to this extreme degree, even though everyone is. People like to pretend no one is going out on dates with multiple people, even though they are. People are not interested in the reality of their dating world.”

He says the experience “pushed my personal tendencies to overthink everything to kind of huge extremes. Maybe there’s interesting insights in what I tell you, but a lot of it is my brain chasing its tail at higher and higher extremes. Something tells me I’m not going to change this, but I think I need to take it a lot easier.”

Dana Neil liked the adventure of participating in Dating Diaries. “Sometimes it feels like a big deal to put yourself out there, but it’s really not,” says Dana, who also learned she acts differently depending on the potential she sees in a man. “When we first started, I had met Florida Guy. It was always casual. I think differently for a casual relationship. If I see red flags with someone I think has more potential, I handle those earlier, but if I’m dating someone casually it doesn’t really matter.”


Michael Amesquita thinks dating is a frame of mind and Dating Diaries pushed him out of his dating rut. “Dating can be fun,” he says. “You have to be proactive and control your own dating life.”





The experience made Jenn Heilman analyze her dates more. Whereas she usually tended to get caught up in the date, having to report back on how it went made her think about it more after the fact: “It made me look a lot more for signs about if they’re interested or not. And I thought more about if I was really interested. Is there mutual chemistry or not?”



Kate Searby thought it was an interesting experiment to think critically about her dating patterns and the types of guys she chooses but didn’t like sharing so publicly. It also reaffirmed how important communication is to a relationship. “Life is too short to not say exactly how you feel and exactly what you want,” she says. “It’s easy when you start dating someone to play it cool and not express your feelings.”

It also made her realize what she wants in a man: “There have been a couple of guys that I’ve dated, like Republican Guy, who were so smart and handsome, but I knew in my heart that it wasn’t right for me. I really do need to be with someone who does care about the world and wants to make a difference, but I still went out with these other guys who were in real estate or investment banking. Not that you can’t care about the world in those careers, but those guys made it clear that they were doing it for the money. I think that was a red flag that I ignored.”

Lucas Wall thought the experience was good in focusing his attention on dating and making a concerted effort with it. And he liked reading the other diarists’ updates and the roundtables. “It reminded me that we all struggle with similar things,” says Lucas. “It doesn’t matter if you’re heterosexual or gay—there are other people dealing with these same issues. Dating is a challenge, and it has to be something you’re active in doing. You have to be really out there.”

For Lucas, the roundtables were really helpful, particularly the dealbreakers question. “It had lot of direct impact for what I was dealing with at the time,” he says. “You can’t expect to meet someone perfect, but you have to understand there are some basic compatibility issues. Someone could be perfect in a lot of areas, but there are a few I just can’t see overcoming. I can’t continue down the road and think we’ll magically overcome these issues. I want a lifetime partner. I’m not in the dating pool for a fling.”