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Dating Diaries Roundtable

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

After how many dates do you start to consider it serious? When is it time to have that conversation with your date?

Dana Neill: It’s not the time frame; it’s the feeling you get from the other person. But it’s definitely not after the first date or the second and maybe not even the third. I think you know pretty early on if you want to be serious with someone and maybe even earlier if you don’t. If you’re doing things together on a fairly regular basis and you call and e-mail often, then you might start to consider having the “exclusive” conversation. It’s best to say how you feel and let them respond. I like saying something like, “Spending time with you has been so much fun, and I’m not interested in seeing other people.”  If the other person feels the same way, then they’ll let you know. If they don’t, then you get to decide if you want to move on, or maybe they need a little more time.

Michael Amesquita: Well, it’s been a while, but I’d have to say that after a few exclusive outings without others present would be the point to have the “are we a couple?” talk.  I mean, your friends see you all touchy-feely and they’ll have questions, so it’s best to know the answers even if you both decide not to define the relationship. 




Max Schwartz: I think the kinds of dates matter more than just the number. I think it’s possible to go on a number of low-key drinks/happy-hour/coffee dates or even dinner dates and still be not very serious. But if your dates are getting more elaborate or more intimate, that’s a signal. And maybe after a few of those it’s time to have a talk. But hey, I’m not always that good at this. I’ve gone the entire length of things that I’d consider relationships and never had the relationship talk at any point—probably a mistake on my part.


Kate Searby: There’s no set number of dates that magically transform a new relationship from casual dating to serious. I much prefer to take things slowly and live in the moment. Life’s too short to stress over the “are we or aren’t we a couple?” question. When it’s right, it’s right. No label necessary. If I’m enjoying his company and he’s enjoying mine, we’ll naturally spend more time together. That’s what counts. I don’t understand the urgency of defining a relationship early on when you’re still getting to know each other. It’s better to let relationships develop organically and go with the flow.

Lucas Wall: If somebody can last ten dates and six weeks, then I start to think of him as a boyfriend prospect. A couple more weeks and it’s time to have a conversation about being serious/exclusive—around the two-month point seems natural.

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