10 Worst People You Can Have a One Night Stand With!

A one night stand can be liberating and sexy. But if you’re having it with any of these 10 kinds of people, it could turn into a nightmare instead!


One night stands can be fun, reckless, or completely regrettable.

And if you’re one who isn’t against one night stands or lusty affairs, it’s an exciting opportunity to try something new, just as long as you keep the dangers of casual sex in mind and remember to protect yourself.

A no strings attached night of fun can be a mental stress reliever and a great way to enjoy a guiltless night of sexual fun without the consequence of a long term relationship.

But are you really ready for casual no strings attached sex with someone you barely know?

The thought may seem exciting or easy to handle, but you need to know that casual sex isn’t for everyone, especially the ones who have a hard time separating emotional sentiment from sexual excitement.

[Read: 10 casual relationship rules to keep sex just casual]

But if you’re up for a wild night of fun, love sex and hate commitments of any romantic kind, then perhaps, a one night stand can be a perfect way to indulge your sexual side.

Those sexy one night stands that end up not-so-sexy after all!

As good as a one night stand may seem, there are occasional circumstances you may come across that can ruin the night and several more days to follow.

Have you ever found yourself getting into a fun sexual experience with someone one night, only to bury your head in shame the next morning and regret it for a long time to come? [Read: How to make the morning walk of shame feel more respectable]

If you’re in a loving and committed relationship with a partner, of course, you’re not going to experience too many of these horny mistakes unless you’re an adulterous pleasure seeker.

But if you’re an occasional one night stander, chances are, you may hook up with someone without thinking twice about it, and eventually sink your head into the pillow of regret the morning after.

An awkward one night stand doesn’t happen all the time, but if you hook up with the wrong person, that one night could come back to haunt you or leave you feeling awkward every time you bump into this person you had a sexual fling with. [Read: 6 sneaky ways to kiss a friend accidentally and get away with it!]

10 worst people you can ever have a one night stand with!

If you’re single, there’s nothing wrong with having guiltless sex with someone, be it a sex buddy or a friend with benefits. But before you jump into bed with someone, always make sure your one night stand won’t come around some other day and bite you on your backside!

You could enter into a one night stand without worrying about the consequences, but keep these ten people in mind and avoid bringing them back to bed with you. The consequences may be a series of guilty moments, awkward moments or moments that make you wish you were invisible!

#1 Your ex you still love. Exes are always dangerous ground. They’re like a stroll in a minefield where you just can’t predict what could happen. Sometimes, it may help you realize you just don’t have feelings for them anymore.

But almost all the time, having a one night stand with an ex you bump into could unshackle those hidden and subdued feelings of love that you thought doesn’t exist anymore in your heart. You or your ex could end up falling in love, or you may find yourself in a confused on and off relationship that’ll leave you feeling worse than ever! [Read: 14 things to keep in mind to feel awesome when you bump into your ex!]

#2 Your best friend. A best friend *of the opposite sex* is someone who knows you very well. Both of you may have flirted and teased each other, but yet, neither of you have ever crossed the line. But if you get into a one night stand with your best friend, your friend may feel disrespected or confuse the experience with chemistry or love!

Once you sleep with a friend, there’s always going to be an awkward feeling when it’s just the both of you. And it may eventually lead to both of you hooking up or drifting away forever. Are you willing to risk those long years of friendship over a few mindless moments of lust? [Read: Why guy best friends are nothing but trouble for all girls!]

#3 Someone who’s married or taken. No strings attached sex is the kind of sex you have where there’s no emotional baggage or feelings involved. But when you have sex with someone who’s married or taken, you’d always feel guilty about it because you were the other lover, even if it’s just for a night. [Confession: I slept with a married man and paid the price]

And if the person you slept with isn’t happy in their own relationship, they may pursue you or seduce you in the hope of seeking lusty happiness from you, and getting away from their own miserable love life at the same time. Before you know it, you may find yourself trapped in a confusing and painful love triangle. [Read: Love triangles and its confusing complications]

#4 Your boss/coworker. Firstly, most offices have clear rules about office romances and it’s almost always frowned upon. So if you have a fling or a one night stand with your boss or a coworker, it’s something you can’t get away from. The word may spread, the person you slept with may expect more, they may sexually harass you, or even spread rumors about you when you don’t play along with their requests or sexual desires.

There are so many scenarios where things can turn bad in an office fling, and there are very few happy endings there. Want to take a safer bet? You could look for love in the workplace, but avoid the office one night stand for your own good.

#5 Your friend’s lover. The thought of seducing your friend’s lover can seem pretty exciting, especially if you love winning. On the other hand, if your friend’s lover discreetly tries to flirt with you or get touchy feely now and then, you may even be secretly flattered and excited by it.

But no matter how arousing the idea seems, avoid it because the word always gets out at some point of time. Not only are you stabbing your friend in the back, you’d also be shunned by everyone else, and you’d be named the friendly whore too. Would you really feel comfortable if all your friends try to keep their partner away from you because they don’t trust you? [Read: Things you need to know before hitting on a friend’s girlfriend]

#6 A relative. When you’re tipsy or reckless, it’s easy to make a horrifying mistake, and that includes the incestuous one night stand. Do you have the hots for a cousin or a far relative? However distant they may be in the family tree, avoid one night stands with a hot relative because it’s far too risky, not to mention, unethical in most parts of the world.

#7 Your crush. Unrequited love sucks. Do you really want to make it worse for yourself by bringing sex into the equation? If you’re crazy about this person, and find the perfect excuse to get them to bed *a wild party and lots of booze*, it may seem like the right opportunity to get sexually intimate with them. [Read: What is unrequited love and how can you get over it?]

But when they wake up the morning after and move on, you’ll be the broken hearted one lying in bed wondering why your crush doesn’t love you back. You’d feel worse, and now that you’ve had sex, you’ll feel more intimately attached to this person. You’ll have a harder time moving on, and you’ll feel wretched because your crush may even avoid you. Can you handle that?

#8 Roommate. A roommate is someone you live with, not sleep around with. Of course, given the right circumstances, true love could bloom if both of you are looking for it. But if you get carried away in the heat of the moment and try to use a perfect excuse to have sex with your roommate, things could just go from awkward to extremely weird the morning after. Remember, both of you live together and have to see each other’s faces every day. [Read: How to make a sexy and successful booty call to a friend]

#9 Someone who has a crush on you. Just like how having sex with someone you have a crush on is bad for you, having sex with someone who has a crush on you is just as bad. Not only would you leave this person pining over you and trailing you like a lost lamb, the person you sleep with may also turn possessive or try to force you to sleep with them again.

And no matter how many times you walk away from this person, they may still pursue you or try to convince you to date them. [Read: 10 ways to reject a guy you don’t want to date in a nice way]

#10 Your arch enemy. As much as you hate your enemy, there’d always be a small part of you that respects them *which is why you see this person as a threat and hate them for it*. If you’re forced into a situation where you have to spend time with this person, there could be an occasional chance that things may end up in a one night stand. [Read: How to pick the right guy for a one night stand and initiate the conversation]

The night may start off with hate, which could turn into admiration or awe as the night progresses. Add a few drinks into the equation and you may even be lusting for this person before the night is over. But as keen as you may be to get into bed with this person, avoid jumping into something like a one night stand with your enemy. [Read: 6 tips to recognize a girl who wants to hook up and 12 ways to hook up with her]

You don’t know if you really like the person or it’s the circumstances that’s leading you to do something you may come to regret in the morning. If you do find yourself falling for an enemy, meet them a few times before sleeping with them. You’d feel terrible if you wake up and realize it’s a mistake, or worse, you’ve been tricked into sleeping with them!

[Read: How to get a friend to have sex with you by planning it right]

One night stands aren’t all bad as long as you protect yourself. In fact, they can even be really fun. But just remember to avoid having a one night fling with these 10 kinds of people, or you may wake up with more than just regret, possibly a really bad memory that you can’t ever erase!

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Cheryl James
A lover of bad ideas and a true romantic at heart, Cheryl James hates excuses and loves integrity. She believes that one day can change everything and wakes up ...