Planning The First Sleepover

Men's Dating

Planning the First Sleepover

Kara Pound

Written by: Kara Pound

Kara Pound

Kara Pound is an award-winning journalist based in St. Augustine, Florida. She holds a bachelor's degree in journalism from Flagler College. Her work has been published in INKED, Natural Awakenings, Design Aglow, Memphis Flyer, Jacksonville Magazine, E/Environmental Magazine, and dozens more. Check out some of Kara's work at

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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It’s tough to gauge when a new relationship is ready for an overnighter. If you haven’t sealed the deal, a.k.a. bedded each other, then it’s safe to say you’re not ready. If you’ve shared a toothbrush and are comfortable with each other’s bodily functions, then try planning a trip together. Just choose wisely. Here’s a breakdown of the good, the bad and the ugly when it comes to overnighters in a new relationship.


If you want to see how your new girlfriend handles not having a blow dryer or running water, then take her to the great outdoors. Camping is a real but dangerous way to get to know someone. Your plan of s’mores and Jiffy pop could ultimately blow up in your face. Stock up on plenty of toilet paper, and remember that sleeping under the stars can test a relationship.

Bed and breakfast.

While they’re quaint and intimate, a bed and breakfast is not always the best way to take a new relationship on the road. At these establishments, you’re pretty much staying under someone else’s roof. The owners are hands-on and like to chat. If you’re looking to get to know someone, a B&B may not have the most privacy.


 “Look at where you and

your partner stand.”

Road trip.

You might think of a road trip as something you do with a group of friends. But if you’re looking to get to know your new girlfriend, a road trip can bring with it unsuspecting experiences. Imagine just getting in the car and driving to the biggest ball of yarn or stopping at South of the Border for a few arcade games. A random road trip can be the best way to get to know someone.


Our verdict is that for a new relationship, play it safe and opt for a hotel in a hip, happening city. Depending on where you live, choose a place that’s about a two-hour drive. Look at local, second-tier cities like Biloxi, Asheville, Oakland, Tacoma or Albuquerque. In this case, the bigger is not necessarily the better. Also, make sure to have an idea of museums to visit and restaurants with high ratings.

If you’re planning your first overnighter, look at where you and your partner stand and consider some of these four good and not-so-good places. If you haven’t had a successful dinner without awkward silence, what makes you think a weekend away will be any different?

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