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How to Approach Sleeping Over at Her Place Like a Gentleman

For one reason or another, dates tend to happen at night. 

While some people might try to have a daytime first date over coffee or a walk in the park, the dominant cultural script we have for dates (dinner, movie, bar) is one that begins some time after 5 p.m. and winds its way through the course of the evening. 

Meaning, if you’re having sex with your date, it’s probably late at night. And there’s a good chance that may lead to one person sleeping over after the hookup. 

Now, in some cases your date will be sleeping over at your place, but especially for men dating women, they’re often invited over to their date’s place rather than vice-versa. 

Why? Well, many women will feel more comfortable in their own home. Being alone with a man they don’t know very well yet can be a bit scary, and having the interaction play out on their turf is more likely to set them at ease. (Also, let’s be real, most single guys don’t have very appealing living situations.)

Regardless, that first sleepover — whether it’s happening the night of the first date, the first hookup, or later on — can make or break a fledgling romance. 

Out on the town and dressed nicely, people might be able to put up a bit of a façade, but in a more domestic setting, fresh from having sex, it’s easy to let your guard down and show the real you — and if that’s not someone your date is into, things could be over in a hurry. 

In order to help you pull off a relatively mistake-free first sleepover, here are some dos, don’ts and expert tips from a selection of dating coaches and psychologists. 

1. What to Do When Sleeping Over for the First Time

The most important thing to keep in mind when sleeping over with a date is that their experience matters, too — and how they feel about things could impact whether you ever see each other again or not. 

“It’s not just about you and what you’re hoping for,” says Tina B. Tessina, Ph.D., psychotherapist and author of “Dr. Romance's Guide to Finding Love Today.” “Your date will also have expectations, and they may not be compatible with yours. If you’re hoping for a relationship, what you do tonight (and after) can make or break the deal.”

To that end, Tessina suggests being generally kind and courteous. 

“Be amiable, but not overeager,” she says. If you’re dating a woman, you have to consider that she might not be used to having a man in her space. “Women are often feeling fragile on this first sleepover, so take it easy. Mind your manners.”

She also adds that if you’re invited over directly, rather than after going out together — such as being hosted for a romantic dinner, perhaps as a second or third date — that bringing flowers isn’t a bad idea. However, whether that’s the case will depend on your age — younger generations might be weirded out by such an overt display of traditional courtship. 

Meanwhile, Connell Barrett, the founder of Dating Transformation and a dating coach with The League, says you should try to take the sleepover seriously — even if the relationship isn’t yet. 

“The morning after, you want to make your date feel great about the decision they made — to take you into their bed, to be intimate,” he says. “While you’re not in a relationship yet, treat them like your partner, not a hook-up. Whisper sweet nothings, spoon, talk, tell them how great last night was.” 

However, the best way to get an idea of how to be the perfect houseguest? According to Jor-El Caraballo, a relationship therapist and co-creator of Viva Wellness, it’s not to make too many assumptions. 

“Ask, ask, ask,” Caraballo says. “Every person desires different things, so there is no one ‘right’ way to show someone that you're a gentleman.”

“As a general rule, it's nice to be polite and treat people with courtesy, but if it's not genuine and coming from your heart, chances are your date can feel that,” he says. “Either they'll dislike that and let you know or won't consider your gentlemanly efforts important and just move on. The golden rule — ‘treat someone how you want to be treated’ — is a good place to start, and with periodically checking in for affirmative cues you can be sure that you're on the path toward making a good impression.”

2. What Not to Do When Sleeping Over for the First Time

When it comes to things to avoid, there are also a handful of those to consider. For starters, it’s important not to treat the experience with a ‘been there, done that’ mentality, says Barrett. 

“A big mistake is treating it in a casual, transactional manner,” he notes. “Don’t bounce at the crack of down with no more than a curt ‘bye.’ That makes the other person feel used and means you likely won’t be spending a second night at their place.”

As for concrete specifics to consider, Tessina notes that creating a mess and having poor bathroom hygiene are big don’ts, particularly for a female date. 

“Be tidy in her place. Don’t leave your stuff all over,” she says. “If you use the bathroom or shower, make sure you leave it neat.”

Caraballo agrees that a guy’s use of a woman’s washroom can be a tricky hurdle to clear. 

“Don’t leave the toilet seat up,” he advises. 

As well, if your date has roommates or lives with family, it’s important to be conscious of that. 

“Ask how you should behave in accordance with their house rules (maybe don’t walk around to the bathroom in the middle of the night, etc.),” Caraballo suggests. 

Another good tip is to not be too demanding or over-assertive. You might be used to sleeping in a certain way, but in a new space, it’s a good idea to let your date set the tone in terms of how things function. 

Of course, you can make requests — think something like “Is it cool if we leave the fan on? I get overheated easily at night” — but being insistent or simply doing what you want may leave your host feeling uncomfortable or annoyed. 

As before, the guiding principle here is courtesy. Regardless of whether it’s a cramped apartment or a sprawling multi-story house, their home is their space and inviting you there is a bit of a gamble — so treat it (and them) with respect. 

3. Coming on Too Strong vs. Seeming Too Distant

One potential conundrum of sleeping over for the first time is that it can be a very intimate moment. 

Sleeping in the same bed with someone implies a certain amount of trust, and it’s something that we traditionally associate with married or long-term couples. However, if you’re just starting to date, you likely don’t know each other very well — and that can make for an awkward mismatch. 

If you lean into being romantic and affectionate, it might send the other person a signal that you’re very serious about them, even if you aren’t; alternately, if you intentionally put the brakes on things like post-coital cuddling and pillow talk, they might think you’re rude, distant or uninterested. 

The best way to deal with that uncertainty, according to Caraballo, is to be communicative, rather than overconfident about what your date is looking for. 

“I think the biggest mistakes guys (and really anyone) can make is making assumptions about what's supposed to happen or not happen next,” he says. “While I know many people frown at the idea of being explicit in communication, it's always helpful to check in with your partner to make sure that they’re feeling comfortable and that you know what their expectations are and if you can meet them.”

Barrett agrees that being open to communication is important — and notes that you should focus on ensuring your host doesn’t feel like you’re just using them for sex. 

“Be present to how your date’s feeling and don’t overdo this, but let them know that even though this is casual, it’s about more than sex. They want to know you like them for who they are.” 

4. How to Handle Leaving in the Morning

One of the most important aspects of a post-hookup sleepover is how it ends. 

Why? Well, that’s the last time you’ll see each other for a little while — it could be just a few hours or it could be weeks. Or, if things go badly, it could be for good. 

If your time together has been going well but you botch the ending, that could leave an unpleasant aftertaste in your host’s mouth, as it were, and change their perspective on how they feel things really went. But by the same token, if the hookup was only so-so, you can still potentially turn things around by nailing your departure. 

Tessina suggests planning for the morning after the night before — that way you have some kind of plan — rather than just deciding what to do when you wake up. 

“If you have to leave at a certain time, let your date know the night before,” she says. “Don’t just rush out.”

Barrett agrees that discussing the morning strategy before you fall asleep is a good move. 

“If you’re not sure you’ll want to lounge away the morning with your date, the night before, say that you’re meeting a friend in the morning,” he advises. “This way, if you both want to have a long, lazy sleep-in and spend more time together, you can always say you moved the appointment. And if you’d rather get going sooner, you can bounce without any bad feelings.”

That being said, if things are going well, Tessina suggests sticking around for anything your host offers, like coffee or breakfast, and potentially re-initiating some of last night’s physical affection, like kissing or hugging, and telling them you had a great time the night before — unless you didn’t.

“If it wasn’t wonderful for either of you, then say something like ‘I guess that didn’t go so well,’” she advises. 

Caraballo suggests taking what, if anything, you know about your date’s personality into consideration when you wake up the next morning and are wondering how to proceed. 

“This is highly subjective, and obviously pretty tricky territory,” he says. “If you haven't talked about the morning plans before the sun rises, I think the best bet is to be honest in your exit.” 

What does that imply, exactly? 

“Do what feels right for you, and consider what feels like a reasonable and ethically compassionate exit, given the interaction,” Caraballo explains. “Does your date seem like someone who you appreciate a simple note left? What about a wake-up kiss? It all depends on the mood, but take the circumstances into consideration.”

One thing Barrett cautions against in particular is staying too long — a scenario which can make people too shy to ask you to leave or feel trapped in their own home, especially if they weren’t expecting you to be there initially.

“Don’t overstay your welcome,” he advises. “Your date might have things to do. Ask them first thing in the morning, ‘What’s your day looking like?’ They may have somewhere to be. If they don’t and you want to enjoy more time with them, suggest taking them out for brunch, coffee or doughnuts.”

Even if you don’t go out somewhere together, ending on a high note is a good idea, Barrett adds. 

“Leave your date feeling great,” he says. “If you want to see them again, tell them.”

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Alex Manley, Khareem Sudlow