Too Soon to Sleep Over?

Dear Em and Lil,

How soon is it a good idea to first stay over at a new guy’s house that one likes? And what are some topics of discussion/conversation to bring up when getting to know him? In case of lulls in conversation!

-Sleepover Curious

EM: I believe that it is important to keep the end game in mind when you are making small choices. Are you looking for a boyfriend, husband or long-term partner? Hold off on the sleepover! Are you looking for a hookup buddy? Go for it as soon as is comfortable.

I hate to say it but it’s true!

Sleeping over sooner will imply that you aren’t looking for something serious. People prize things that are scarce: diamonds and rare first edition copies of books. This also applies to people’s time; when you give it away freely, you send the subtext that it is worth less than when you share it sparingly. Keep your end goal in mind when deciding to stay over… and in all other dating matters! 

I’d like to apologize for the fact that I sound like a conservative men’s rights activist. Sometimes advice just comes out that way a little bit.

Read on for Lil’s conversation topics!

LIL: Personally, I don’t take Em’s rule as a given. Staying the night early on doesn’t necessarily condemn you to a “non-serious” relationship. On Bachelor in Paradise, one of Em’s and my greatest influences, people fall in love very quickly. Why? Arguably because they log 24 hours a day together! (Also maybe Stockholm Syndrome.) In the non-paradise world, a regular date might last a few hours. But by sleeping over, you’re maximizing the time you can spend with this guy before you both have to go to work.

Listen to your gut as the evening goes on. You can always change your mind, up to the last minute. And it’s perfectly fine to hang out at the guy’s house late into the night and then go home and sleep in your own bed. If you want that security blanket— literal or figurative— take it!

If you decide to wait a little longer, it doesn’t mean that you’re dooming yourself to purgatory or the friend zone. As Em said, it can be a great way to leave him (and yourself) wanting more.

Now, as promised, conversation topics.

  1. Horoscopes and personality tests: regardless of how much or little you believe in this kind of thing, asking someone you’re into about their sign/MBTI is a low barrier of entry way to learn about how they look at the world (i.e. you don’t have to ask them, so Pete, how do you look at the world?) The caveat is, are men into this stuff? I think maybe men are into enneagrams sometimes?

  2. Ask your guy what movie he’s watched the most times. Then, watch it together and let him talk over it as much as he wants. If you watched my movie with me, and then acted interested when I told you how one of the side characters was actually played by Uma Thurman’s stunt double, I’d want you to sleep over anytime!

Conversation lulls don’t have to be scary! Those are great moments to kind of... blink your eyes at him or whatever you’re supposed to do when you’re flirting. Lucky for me, you didn’t ask about flirting so I’ll assume you’re a pro and wish you many happy sleepovers when the time is right!

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