Men's Dating

When is the Right Time to Travel Together?

David Wygant

Written by: David Wygant

David Wygant

David Wygant is an internationally-renowned dating and relationship coach, author and speaker. To find out more about David and all of his dating and relationship-building products, visit

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Let’s say you’re seeing a woman. She’s super cool and you want to take her away. But you begin to wonder…

“Is it too early in the relationship? What is she going to expect?”

I understand. I used to get those thoughts because I love traveling. I especially love traveling with women.

I think it’s one of the greatest things in the world because you get to know a woman outside of her home.

It’s just you, her, a beach, mountains — whatever it might be — for three or four days.

There are definitely expectations that will arise.

If the vacation is successful, she is immediately going to think you two are a couple, so I strongly suggest if you are not interested in her as a girlfriend, you tell her before you travel.

If you want to just go away with her and have fun, you need to state that intention right away.

You need to tell her, “Look, I don’t know what I want and I don’t know what I’m looking for. I know I enjoy being with you and I’d love to go away and have some fun. But I don’t know if this means we’re going to have a relationship.”

Stating it at least gives you the “Hey, I told you so” if she gets too attached and you aren’t ready for a relationship.

Another thing to remember is to keep the initial getaway short. I strongly suggest you go away for a long weekend first before you go away for a week-long vacation.


“Traveling together is one of the greatest

tests to see how you get along as a couple.”

You need to see if you can hang together for 48 hours.

Remember, it’s far different than sleeping over at her place.

You’ll see what her habits are, how often she answers the phone, how she pays attention to you, how consistent she is with her affection and all other types of things.

Traveling together is one of the greatest ways to figure out if you guys are meant to be connected together for the long term.

So if you can pass the weekend test, then plan a week-long vacation. After that, go on a two-week adventure.

Do it in baby steps.

See whether or not you two are mutually compatible for the long run.

It doesn’t matter if you’ve been dating for a week, two weeks, a month or two months, traveling together is one of the greatest tests to see how you get along as a couple outside of the “real world.”

Do you guys have any good travel stories to share with us today? Any nightmare trips? Any vacations that didn’t really turn out to be everything you thought they’d be?

Share your stories with me today. I’d love to read about them.

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