Choose a discreet bag. You don’t want to seem like you’ve prepared to move in for a week; but you’ll likely want a few essentials to make the morning after easier. You’ll also want to be able to brush your teeth and remove any makeup if you wear it.
See what you can fit in whatever bag you usually carry with you. If you normally carry a very small clutch or wallet, you’ll need to bring something slightly bigger or only pack the bare essentials.
If your boyfriend lives far away and this is part of an overnight trip to visit him you can get away with packing a lot more. After all, you’ll need everything you would regularly travel with.
Pack for your nighttime routine. You probably don’t want to get into the awkward situation of having to ask to borrow a toothbrush, but simply choosing not to brush your teeth can be awkward too. Pack anything that you simply can’t live without.
You may want to bring makeup remover if you wear makeup. Some women would rather go to bed with their makeup on than have their boyfriends see them without it. However, this can be bad for your skin, and if he’s your boyfriend he’s going to see you without makeup eventually.
Pack anything you’ll need for dealing with your hair. Some women need to tie their hair into a rag at night but choose not to when they stay with a boyfriend. Of course you’re not going to put your hair up in curlers on this special night, but maybe you want to pack a brush, comb, or detangling spray.
Pack anything for the morning after. There’s a long list of things people bring with them in anticipation of the next morning. Think about what you’ll need for your morning routine and how long you think you and your guy will hang out before you head home.
If you're an early riser, bring your phone charger and a book or magazine. That way, if you're awake well ahead of him, you can keep yourself entertained if need be.
If they fit in your bag easily, you might want to bring a pair of shoes that are easier to walk in than your date shoes.
Don’t forget any medications that you need to take regularly.You can’t be sure what time you’ll be getting home in the morning.
Pack protection if you need it. If you plan on being physically intimate, bringing condoms is always wise. Don’t assume your boyfriend will have condoms at his house. Bring your own. If you're not sure whether or not you'll be having intercourse, bring some along just in case.
Condoms are the only birth control method that also protects against sexually transmitted infections.
Bringing lube or any other sexual accessories you like can be a good idea, too.
Bring cash. This is a good rule of thumb any time you plan on going out for the night. In case things go awry or you haven’t made plans about how you’ll get home, it’s good to know you have some contingency cash on hand for emergencies.
Cash is good to carry in case you both decide to spontaneously go out for drinks or ice cream or breakfast. You can’t always assume he’ll be paying.
Wear a versatile outfit. You may end up spending the morning or even most of the day with your boyfriend. If you went over to his house in a very confining outfit or something only appropriate for a late-night date, you’ll probably feel uncomfortable walking around the park the next morning or grabbing a casual breakfast in that.
It’s great to keep some items in your wardrobe that you feel sexy in but that can be easily thrown on in the morning.
Know what you want. This is the first thing to consider when deciding what the first night together will entail. Don’t assume that just because you’re sleeping over for the first time you’re obligated to have sex. However, if that’s what you’re hoping for, plan for it.
Having sex can be a way of bringing you two closer together and forming an even more intimate bond.
Sex can also bring up tricky issues such as questions about monogamy, sexual history, sexual health, and potential pregnancy. If you’re not up for talking about these things with your guy, you may not be ready for the responsibility of being sexually active with him.
It’s okay to feel ambivalent about sex, especially the first time. If you aren’t ready to make a decision right now, that’s okay. Just make sure that you’re able to make a fully informed and consensual decision in the moment if sex comes up.
Talk to your boyfriend about expectations. This might feel awkward at first, but it’s a conversation that will come up eventually. There are a number of ways you can ask about your boyfriend’s expectations while still being charming and even flirtatious.
If you want to keep the conversation flirty, you can ask what the sleeping arrangements will be. Say something like, “So, do you think we’ll be sharing a bed or should I bring my own sleeping bag?”
If you want to be more direct, you can say something like, “I know we’ve never had a sleepover before. I’m really excited, but I’d also like to talk about each of our expectations for the night. I’m wondering how you feel about sex and if you think we’re ready.”
If you already know exactly what you want and feel certain about it, you can simply start with that. Say something like, “Hey, I’m really excited to sleep over, but I want you to know ahead of time that I am not ready to have sex with you” or, “I’m so excited to stay over at your house tonight. I feel really ready to take things to the next level with sex.”
Stay firm but flexible. If you’ve already made a decision for yourself, such as choosing to have sex or not have sex, that’s great. However, sometimes the specific circumstances may influence how you feel and you might change your mind in the moment. That’s okay. Listen to your gut.
You may have not planned on having sex but find yourself feeling extremely comfortable and excited to try it.
You may have planned on having sex, but if you suddenly feel uncomfortable or nervous, it’s okay to change your mind.
Make sure that your decision is based on your feelings, not on pressure from your boyfriend, your friends, your parents, or other external pressures.
Enjoy each other’s company. You may be nervous about spending the night for the first time. However, remember that your boyfriend appreciates you for who you are. Not only that, he’s surely just as nervous as you. Take some of the pressure off by relaxing together and doing things you normally enjoy together.
Your boyfriend is probably nervous about you seeing what his house and room look like. Put him at ease by letting him know anything you like or appreciate about his living space. You can say something like, “I really like that poster you’ve got on the wall,” or, “Wow, this is a great location you’ve got.”
If his place isn’t that great to hang out in, you can go for a walk or a drive. Take your date elsewhere and come back just to sleep.
Do your nighttime routine. This may involve washing your face, brushing your hair and teeth and doing anything else you need to do before going to bed. Of course, at home you may have a more involved routine, but keep it streamlined for tonight. That way, you won’t spend all of your time in the bathroom with your boyfriend wondering what you’re doing.
You don’t need to explain what you’re doing in the bathroom. He may wonder, but that’s fine.
If you usually braid your hair at night or tuck it up in a rag, you might want to skip that for the first few nights you spend together, if you’re comfortable with that.
Prepare to not sleep very well. The first night you spend the night with another person, your brain actually stays a tiny bit awake during the night as a way of keeping you safe. You may wake up when your boyfriend moves around or changes positions in the bed.
Don’t plan to sleep over at your boyfriend’s house for the first time the night before a big day at school or work.
You may need to catch up on sleep with a nap the next day, even if you try to go to bed early.
Wear what you feel comfortable in. If you hadn’t planned on sleeping over, you may not have brought a change of clothes or thought about planning for what you’d sleep in. Even if you did plan, it may not have made sense to bring pajamas or a change of clothes. What you wear to sleep will depend on how comfortable you feel with your boyfriend and your level of intimacy.
If you end up having sex or being physically intimate in other ways, you may feel comfortable sleeping with nothing on at all, or sleeping in only your underwear.
If he lives with his family, you’ll want to sleep in something conservative in case a parent or sibling barges in or you need to go to the bathroom in the middle of the night.
You can always ask to borrow a T-shirt to sleep in. Many guys find that endearing.
Go to bed when you’re ready. When it’s time to go to bed because you’re both tired, it’s time to go to sleep. If you’re sleeping in the same bed, you’ll need to find a comfortable position for both of you. There may also be things that make it hard to get comfortable, such as:
If he snores. You may want to bring a pair of earplugs, just in case!
If one of you steals the blankets or you like very different sleeping temperatures.
If he likes to cuddle and you don’t (or vice versa).
Let him sleep in. If you wake up first, it’s considerate to let your boyfriend sleep in a bit. After all, you’d probably appreciate the same courtesy. If you wake up first, you can either stay in bed cuddling with him or head to the bathroom to complete your morning routine so that when he wakes up you already look fresh.
If he wakes up first, he may head to the bathroom before you’re up to brush his teeth and make himself presentable, too.
Gauge how you’ll spend the morning. You both might want to spend the morning and even most of the day together, but you might not. Hopefully, you already know what your plans are for the day. If you didn’t make plans, don’t assume that you’ll be spending all morning together.
Did you talk about having breakfast? If not, you can suggest something or ask what he’d like to do. You can say something like, “Do you want to make breakfast together?” or, “I’d love a cup of coffee. Is there a good place nearby?”
Does one of you have to go to work or school? If you do, let him know. You can say something like, “I have to be at work in an hour, but I’d be happy to have a quick coffee together, if you want.” You can also say, “Do you have plans for the day? I’m free, but I understand if you’ve got things to do.”
Of course, your boyfriend should care for you and have lots of respect for you, so don’t feel shy about letting him know if you do or don’t want to spend the morning together. You should be able to express your feelings honestly in a healthy relationship.
Leave something behind if you want. This is a fairly common flirtation tip. Even though you’re already in a relationship, it can be a great way to get your guy excited. It can also be a nice way to leave him something that keeps him thinking about you and ensures you’ll see each other again soon. Some things you might “accidentally” leave behind include:
A piece of clothing
A piece of jewelry you always wear
Your toothbrush or makeup
The book you’re reading
The DVD series you’re watching together
Be respectful if he lives with his family. If he lives with parents or siblings, you want to be respectful in their presence. Follow any house rules and behave modestly.
If his parents have specified that you'll sleep in separate rooms or beds, follow that rule. It could be disastrous if they happen to see that you've gone behind their backs.
Avoid displaying too much affection in front of his family. You can of course be sweet to each other, but avoid kissing or petting each other in front of family.
Dress modestly for sleep and around the house. Don't get up to go to the bathroom in a T-shirt and underwear, for example.