Great 1st Date, but He Might Still Be Stuck on His Ex

Demetria Lucas D’Oyley
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Dear Demetria:

I went on a first date with a guy and had an amazing time. We talked until the restaurant was literally closing on us. The next day, he says he wants to be up front with me, so it doesn’t seem like we are starting with a lie. When he and his ex-fiancee were together, he paid for a cruise, she paid for the plane tickets. They have since broken up and he has moved out. The cruise is coming up and is nonrefundable. Since she is insisting she is still going on the cruise, it’s a dilemma. Should I cut my losses now before I get into this guy or respect his open honesty, since he is swearing it will be platonic? —Anonymous


You had an amazing first time, you like him and you want this to work out, so you’re trying to give it a shot and be willfully naive. I’ll get to that in a second.

I respect him for being up front, as opposed to disappearing for a week and not calling, or telling you he’s traveling and lying about who he is with. Even though it would result in far fewer questions in my inbox, I appreciate that he told you the truth (sort of) and allowed you to make an informed decision about how and if you want to proceed with him.  

I also have to point out that he’s not doing anything wrong here. You two have had one date and there’s no reasonable expectation that your interactions with him are leading to a relationship. He’s single and so are you. You’re both in the clear to date whomever you want and however many people you like. You should both take advantage of that perk until, or if, there is an agreement to be in a relationship.

That said, you need to be careful here. It’s not clear how long ago his engagement ended, but it’s pretty clear that he hasn’t moved on. The evidence is that he’s going on a trip with his ex. He’s single, but he’s not really available.


I understand that he made a financial investment in the trip and doesn’t want to lose his money, which is likely nonrefundable. But when you’re done with a relationship, you don’t create an opportunity to rekindle with your ex, especially not on a multiday, close-quarters trip. You take the loss as part of the lesson learned and you stay home. He’s saying the relationship is over, but his actions say otherwise.

The trip is platonic? Please. They booked the trip when they were in a relationship. They didn’t get separate rooms or separate beds. And have you ever been on a cruise? Even the so-called good rooms with the windows and balconies are teeny. He’s going to be laid up snugly with his ex—someone with whom he was in love and to whom he is very attracted, given their former engagement—in a teeny bed every night for the duration of the cruise. Does that sound platonic to you?


During the day, do you think they’ll spend their time talking to strangers or to each other? When they dock the ship, do you think they’ll be wandering around some hot, romantic locale separately or together? And, after an all-day open bar, heading back to the teeny room and the tiny bed, do you think they’re not going to have sex?

Don’t be naive.

Tell him that you appreciate that he’s being honest, but it’s become clear to you that things are unresolved with his ex. Remind him that you had a great time on the date, and that if ever he wraps up his last relationship, you’d be open to seeing him again when he’s single, and also emotionally available to get to know you. In the meantime, find someone who is single and isn’t hung up on the past. 


Demetria Lucas D’Oyley is a contributing editor at The Root, a life coach and the author of Don’t Waste Your Pretty: The Go-to Guide for Making Smarter Decisions in Life & Love as well as A Belle in Brooklyn: The Go-to Girl for Advice on Living Your Best Single Life. She answers your dating and relationship questions on The Root each week. Feel free to ask anything at

Previously in Ask Demetria: “My Married Friends Aways Invite Their Husbands When We Hang Out”

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