Ready For A Sleepover Date?

Attention divorced daters: Before trying an overnight with your new sweetie, take a tip from men and women who’ve been there.

By Chelsea Kaplan

f you’re recently divorced, chances are it’s been a while since you’ve been with another person in the Biblical sense. However, now that you’ve decided to get back on the dating horse, your first post-divorce overnight date may only be a matter of time. If the idea of spending the night with a new flame makes you nervous, check out these tips from singles who’ve been there. With their helpful hints, your nerves will be calmed before you hit the (unfamiliar) sheets.

Tip #1: Read up
“I was so nervous about sleeping with someone again after all those years of
“I met my most supportive friend first for a pre-date pep talk.”
sleeping with the same person that I went out and bought this book called Sex Tips For Straight Women from a Gay Man! My moves were pretty rusty, but I think this book got me right back on track. My boyfriend at the time certainly wasn’t disappointed by my playing catch-up!”
—Tamara, 35, Washington, DC

Tip #2: Ease up
“After I split from my wife and met someone I was ready to get intimate with, I was so psyched for it to actually happen. I had been putting so much pressure on myself for this night to be amazing, and my friends were all really pumping me up for it. In my mind, I had convinced myself that it had to be incredible and more importantly, that I had to be incredible for her. Well, once it came time for everything to happen, I wasn’t exactly up to it, if you catch my drift. I think I was just too nervous and anticipatory. My advice is to really go easy on yourself and not stress yourself out—nothing good happens when you do the opposite!”
—Roger, 30, New York, NY

Tip #3: Suit up
“Before the evening I knew that my then-boyfriend and I would first spend the night together, I went out and bought about $200 worth of lingerie from Victoria’s Secret. Even though I was fairly nervous, I figured looking like I was confident would help me feign a little courage, and it did. My boyfriend was pretty pleased too, so everybody won.”
—Michelle, 29, Atlanta, GA

Tip #4: Groom up
“I made the mistake of not shaving my legs prior to my first post-divorce sleepover, even though I knew what my boyfriend had planned for the evening. I guess I was just so used to being in marriage-mode and not having to get all gussied up for my ex-husband that I went into this new experience without doing so either. Well, when I got into bed with my boyfriend and eased myself up next to him, he was like, “Whoa!” My prickly legs definitely didn’t do anything to set the right mood. The sleepover still happened, but I was so mortified the whole time that I don’t think I enjoyed it as much as I could — or should — have. I learned my lesson to take some time to primp before a big date.”
—Kristy, 34, Brookline, MA

Tip #5: Lighten up
“I wanted to create a romantic atmosphere in my bedroom before I had a new woman stay over for the first time after my divorce. I figured the best way to do it was with candles, but not so many that it looked like I was deliberately trying to set up a huge
“A glass of wine helped calm my nerves.”
seduction scene. I just purchased a couple of nice-smelling ones at this local gift shop and began burning them about 30 minutes before my date came over. It smelled fantastic, and it didn’t look like I was setting a scene. That little bit of effort went a long way for both of us.”
—Timothy, 33, Long Boat Key, FL

Tip #6: Listen up
“Before my first post-divorce sleepover, I was pretty freaked out! I knew it was going to happen, but it had been so long since I was in that situation with someone other than my ex that I felt like I knew nearly nothing about sex! To calm myself down, I called my super-supportive best friend and told her I needed a pep talk. We went to dinner, and she spent the entire meal boosting my confidence and telling me how fabulously wonderful and sexy I am and how I was going to just knock his socks off. All of her encouragement definitely made me feel more confident, and I went into the evening feeling much less apprehensive.”
—Claire, 40, Phoenix, AZ

Tip #7: Drink up (but not too much!)
“I’m not suggesting you get drunk before your first sleepover — that would be a big mistake — but having just one glass of wine will mellow you out a little bit and calm your nerves. It worked for me—and for all of the friends I’ve advised to do the same.”
—Dierdre, 33, King of Prussia, PA

Tip #8: Don’t fill up
“The night I knew I was going to sleep with a woman again for the first time after my divorce, I planned this big, romantic evening that first involved going out to this incredible restaurant. My date and I ate and drank so much that by the time we got home, all we wanted to do was just lie on the couch and moan, we were so full. Needless to say, the romantic evening I had planned never happened. Word to the wise: Prior to that first sleepover, don’t stuff yourself!”
—Harry, 35, Highland Park, IL

Chelsea Kaplan is deputy editor at Her blog, “I’m Somebody’s Mother?” can be found at
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