LA: I mean, you’ve done so much now that you’re even making a show about it, but I want to go back to that first trip you just mentioned where you were 22, where did you go?

TER: Yeah, so the first trip I took was to Pink Sands, a hotel in The Bahamas, and the sand was pink. It was so beautiful. I went by myself and I remember I am still friends with this person. This beautiful man was there with his girlfriend. He was gorgeous. He was much older than me. And years later he said to me, “I thought you were a kept woman,” which is such a gross expression.

LA: And an old-fashioned one.

TER: It’s just a gross terrible expression. But the reason I thought it was interesting is there was a sense of there’s no way I could be on this trip of my own accord, paid for by myself. I was 22, I had just finished my first TV show and I don’t know. It was this glorious trip and I was just busy enjoying my company. One of the things that happens when you’re solo traveling and happened on that trip was it’s like an experiment in, are you comfortable enough to say, “I don’t know what that is. Can you tell me what that is on a menu?” Or to be uncomfortable enough to be sitting somewhere by yourself.

And I always tell people who are like, “I don’t know. I could never go on a trip by myself.” I say, “It might not be for you. However, one of the best ways to start is start by going to dinner by yourself. Start at five o’clock on a Tuesday, but then try going on a Friday or a Saturday night when a restaurant is full and you have to go up to the hostess or the maitre d’ and say, table for one.” And they’re like, “Oh, just you?”

“Yeah.”

“Are you waiting for someone?”

“I am not.” Or you can start by going to the movies by yourself. See how that goes because you will, on a solo trip, you will have multiple table for one experiences.

LA: It’s so interesting when you were describing that and also describing that trip to Pink Sands, and it reminded me of a trip that I did, which was a work trip. So often working at Condé Nast Traveler, I end up staying in these fabulous hotels by myself.

TER: Yes, that’s amazing.

LA: Which is amazing. And I was sitting having dinner on my own at this beautiful hotel, and a man literally shouted across the restaurant, “You alone, why are you alone?” It’s really fascinating to me how even if you start to feel comfortable with yourself, it makes other people uncomfortable.

TER: Other people. Yeah. It is interesting. I mean, I think it’s an exercise in holding your own space for multiple days. And I’ll tell you some of my tips that I do and use. So I have discovered through trial and error that a solo trip for me is no more than four nights. When I shift over into five nights, I start to feel like it works back on myself and I do feel lonely. And now this might change as I get older or whatever, but four days feels nourishing, it feels comfortable. My mind is not a dangerous neighborhood, whereas I flip over to the other side. And so what happens is you don’t have someone to share things with, and so you’re sort of holding your own experience.