Sarah, an old ‘gal pal’ I used to know many years ago said to me once: ‘Dave I can’t believe you did a sleepover. Sleepovers are weird, you actually hold someone in your arms overnight’. ‘So what? I like them’ I responded. I have only done a very small number of sleepovers. A few with someone I almost married long time ago, and only 3 with old SBs. I offered one to someone who, let’s call her, ‘Blondie’ years ago but she said ‘Montrose, both you and I know better so I will politely decline’. She was right perhaps. She was referring to the fact that once you sleepover with someone it may become something more and it also signifies that while you are sugaring the liaison is developing into something more and the two of you have become very comfortable with each other.
Let’s see how my old sleepovers went:
1. The first one was in Texas when I flew over this lady I was seeing in NY. She stayed with me for the weekend which was a mistake. Why? because I feel weird hosting people in general so having someone for 2 and a half days right on top of me was a bit too much. We ended up having a little fight via email when I mentioned that while it was nice there were a few details (like sex) which did not go as planned. I liked it but it could have been better
2. A couple with Serena. Those were the best and I was amazed how open she was to the idea of having one. Interestingly, she broke up after our second one. We hadn’t seen each other for a while, she started seeing someone else, then we had the sleepover, then she gave me a kiss on the cheek and took off. It happens, I guess. Come to think of it, after each one of these sleepovers we broke up
3. The French Moroccan lady in London, ages ago. It was hot, but after that I just wanted to get rid of her,, way too much bubbly personality
4. College: playful and close, and time will tell what happened
So sleepovers are tricky: if you already friends and get along personally, that’s great. If not, then might as well just remaining casual dating partners and skip the whole sleepover idea