17 Hilarious Questions You Need to Ask Your Bestie Right Now

Your best friend is your closest confidant. The one person you can tell your deepest secrets to without the fear of being judged for sharing how you feel. You talk all the time, she has her own ring tone (and text tone) in your phone, you know where everything goes in her kitchen, you consult each other about major life decisions, you know about all her relationships, her favorite foods, what her dream vacation is—you’re entrenched in each other’s lives. Still, no one knows everything there is to know about someone, and that’s part of the fun of having such a close friendship. Being able to confide in someone you trust whole heartedly while also knowing that there’s still something to learn about your best friend (and vice versa) keeps your relationship fresh and fun. These 14 questions can help you learn more about one another while while laughing the entire time.

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17 Your most embarrassing secret current crush

Gushing about her old embarrassing crushes is fun, but why not ask her about her current embarrassing secret crush too? Is she secretly into her co-worker that everyone thinks is a little strange? Does she like one of the wallflowers at the gym? What about her current crush makes it embarrassing enough that she keeps it a secret? What’s so special about him that keeps him on her mind when there are less embarrassing (and possibly available?) guys to crush on? Even if she has no intentions of actually pursuing her crush, ask her who she’s secretly pining over.

16 Where you hide or used to hide your journal

Keeping a journal can be a cathartic experience. Having the ability to write down your thoughts in a raw, unfiltered way can help you to feel better about a stressful situation or just vent when you aren’t sure what your feelings are about a situation. Asking your friend where she hides (or used to hide) her journal is a big deal. Depending upon how private she is about her innermost thoughts, she may have a totally unexpected and hilarious hiding spot, like wrapped up in a gardening pot or taped to the back of her dryer. Just don’t be offended if she doesn’t let you read it.

15 The longest you've ever gone without shaving your legs

Oh the glory of winter months in colder climates where women can more easily get away with not shaving their legs for longer periods of time. While silky-smooth legs feel great, maintaining them is quite a chore. Ask your bestie what’s the longest amount of time she’s gone without shaving and you may be surprised to find it was days (or weeks) longer than you have gone yourself. Maybe she’s got fine hair that doesn’t show as easily, or perhaps she’s just one of those women who doesn’t bother to think about it enough to care if her legs are starting to look manly.

14 Which celeb do you pretend to hate but secretly love?


Who doesn’t have a secret celebrity crush? Celebrity crushes, closeted or stated proudly are great because they allow us to indulge in the idea of a romance that we know will never really happen. With a celebrity crush, we can live out all of our favorite “what if” scenarios that we know are typically only found in rom coms and romance novels. Asking your bestie about what celebrity crush they pretend to hate but secretly love may surprise you. Maybe she’s crushing on an older celebrity who isn’t her type, or someone who’s eccentric or commonly viewed as the friend and not the hottie.

13 Favorite guilty pleasure TV show?


Most people have at least one television show they love to watch but will quickly turn off or feign interest in when other people are around. Guilty pleasure television programs can be anything from a reality TV dating show to soap operas or a sitcom that for some reason makes you feel self conscious about watching. You may be surprised to find that your bestie loves Days of Our Lives or that she’s seen every episode of Rock of Love with Bret Michaels on VH1. Don’t be afraid to share your favorite guilty pleasure television show with her too. You may find that you both secretly like the same shows, or at least give each other reasons to check out each other’s favorites.

12 Middle School Crush?

via miamisburg.com

Middle School is one of the most challenging and awkward times in a person’s life. Not only is your body going through huge changes (thanks hormones!), but socially it’s a brutal time. This mess of hormones and fitting in can make it hard to admit who your crush may be. Even as an adult, there’s a good chance your best friend had a (possibly secret) middle school crush that you never knew about or haven’t met. Find out what they liked about them and if it’s around, pull out that middle school yearbook to get a good look at what your bestie’s crush looked like all those years ago.

11 Weird Turn On?

Personal sexual preferences are a sensitive topic, but turn on’s that others might find weird can make us wonder what others will think. Even if it’s something completely innocent like being turned on by a guy that has a classic 90s style hairstyle with frosted tips and everything, it can feel awkward to think about sharing your weird turn ons with other people. This is why your best friend is the perfect person to ask, it’s someone you know will trust you and likely will laugh with you about whatever it is that turns them on. Be sure to tell them what weird turn ons you have too so they won’t feel like the only one with a weird turn on.

10 What’s Your Weirdest Bad Habit?

Everyone has bad habits. There’s a good chance you feel like you know all of your best friend’s bad (and good) habits because of how close you are. While you may spend countless hours together and share most everything, you might be surprised that your best friend likes to eat rocky road ice cream in the middle of the night or that she bites her nails instead of trimming them. Whatever her weird bad habit is (or yours are), be sure to laugh together about your quirky habits. Being best friends means you should be able to share your quirks with a smile on your face.

9 If you had to make an alias, what would your name be?

Who doesn’t like the idea of having a secret identity? The anonymity that comes with being able to be in a place where your name is just a name and isn’t in any way tied to your past is liberating. Even if you’ve never had anything in your past that’s worth hiding, an alias is a fun idea—to be able to go anywhere and be referred to by a name that feels fresh and unique. Would your best friend take on a super hero inspired alias? Or just a name she’s always admired? You may be surprised at what your best friend would prefer to be called if given the chance.

8 What’s the best joke you’ve ever heard?

Laughter is the best medicine. Even when you’re feeling down, a good laugh can lighten your mood and make you feel inspired to see the humor in your day. The Mayo Clinic notes that laughter can wake up your body, reduce stress, and boost your overall mood. Your best friend’s favorite joke may be one you haven’t heard, or even if it’s one you’ve heard before, maybe your best friend has a way of telling it that cracks you up even more. Whether you’ve heard the joke before or not, share your favorites with one another and see which gets you laughing the most.

7 Have you ever burped/farted in front of your date?

Being nervous on those first few dates with a new person are always nerve wracking. You want to impress your date, not embarrass yourself. Still, sometimes you just can’t help what your body does. While this may be mortifying in the moment, it’s something you should be able to look back on and laugh about, especially with your best friend. Ask your best friend about any times she may have burped (or worse, passed gas) in front of a date and how she handled it. Did she say anything? Pretend it didn’t happen? Blame it on someone else? You’ll likely both be laughing at how comical the situation was.

6 What’s your most embarrassing moment?

Embarrassing moments are hard to forget. Who better than your best friend to talk about your most embarrassing moments with? If she’s shy about sharing her own most embarrassing moment, you can try guessing things you know she’s talked about before, just keep it light and fun. Did she forget her speech in front of a large group at work? Trip over her feet walking into a wedding reception? Whatever her embarrassing moment is, laugh with her about it. There’s no sense in letting a bad moment ruin you whole mood. When you and your bestie can laugh at yourselves, everything in life is easier.

5 How many times have you made out with someone while drunk?

Being safe when you go out for a night of partying should always be a top priority, but that doesn’t mean things can’t get a little crazy when you’re out for a girl’s night. Maybe you suspect your best friend had her eye on a certain guy for a reason, or your best friend is a by-the-book type of girl who always follows the rules, so you’re curious if she’s ever had enough liquid courage to come out of her shell and make out with someone while out on the town. Who’d she make out with, and did it ever lead to meeting up after that night?

4 Last lie you told/worst lie you’ve ever told?

Honesty is a great quality to have. Honest people are reliable and easy to trust. Still, everyone lies sometimes (even if it’s just a white lie). People lie for all sorts of reasons, but if you are prepared to know that your best friend may have lied to you, and you’re willing to see the humor in the situation, go ahead and ask her about the last lie she told (or the worst) and why. Maybe she gave someone a fake phone number, faked being sick to get out of work, or simply agreed with someone because it was easier to do so. Whatever the reason was, find the fun in it and don’t get too caught up in the details.

3 The real last time you washed your jeans

You are at the coffee shop with your best friend. As she pulls out some cash from her pocket to pay for her order, she also pulls out a ticket stub to the concert you guys went to last week, and it wasn’t faded from the wash. She tells you she’d just washed them, and they look clean enough, but ask her when the last time was she really washed her jeans. Maybe she doesn’t like how the feel out of the wash, maybe she just hasn’t made the time or doesn’t care to wash them until they’re noticeably dirty.

2 If she actually did rip that shirt you lent her

One of the biggest perks of having an awesome best friend is sharing your clothes. Even if you don’t wear exactly the same size clothes as your best friend, the ability to swap clothing and know it will be well cared for is awesome. The last shirt your lent your best friend was returned and looked fine, until you noticed a rip in the side. When you first asked, she feigned knowledge of the flaw, but you have your suspicions. Ask her again if she did rip the shirt, and you want to hear the (potentially funny) story behind it.

1 An embarrassing sex story she still hasn't told you


Even with your best friend, conversations involving sex can be a big deal. Ask her to tell you about an embarrassing sex experience she’s had that she hasn’t told you about. Maybe she was nervous and tried to do something sexy for her man but instead, fell off the bed, or she read his cues wrong and made moves on him when he wasn’t interested. She may have an embarrassing story from the past or just the other night. While it’s embarrassing when we try to be sexy and things don’t go as planned, but don’t let that stop you from laughing about it now.

Sources: mayoclinic.org

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