Expectations vs. Reality: One Night Stands and Dating a Coworker

Are you thinking of having a one night stand? Maybe you’re thinking of dating that hot young intern? Regardless of which of these you’re daydreaming about, you should first be aware of the realities that come along with it.

As a woman in her mid-thirties, I’ve had my share of the dating world, and let me tell you there are some things that I would certainly tread lightly upon. Two of those things are one night stands and dating a co-worker. Of course, I’ve done both (I even had a one night stand with a co-worker once), but the reality is never the same as the expectations.

One Night Stands: Expectations

Nice elegant couple next to the door

When it comes to one night stands, we have certain expectations that can, quite honestly, be hard for a guy to live up to. We’ve all seen romantic comedies that make one night stands seem so sexy and amazing, but let me give it to you straight: They’re not all they’re cracked up to be. Here are the expectations.

1) He Will Be Awesome in Bed

There’s an unspoken assumption that if you’re bringing home a hot guy just for the sake of sex, he’s going to be awesome in bed. In reality: It really could go either way, so it’s best not to get your hopes too high up.

2) You Will See Him Again

If he is amazing in bed and funny and attentive, you will really want to see him again. The brutal reality, however, is that unless he’s seriously into you, you’re still just going to be a one night stand to him.

3) He Could Be The One

You meet a hot guy at the bar, the chemistry between you is outstanding, and you take a chance and bring him back to your place thinking “Oh my God, he’s totally The One!” The reality: He’s probably not The One. Most one night stands are just after sex, so if you want him to be more than a one night stand I don’t recommend sleeping with him until you’ve at least had a proper date.

4) You’ll Have Amazing Morning Sex, Too!

We all hope that some awesome “night sex” will turn into “first thing in the morning sex” as well, but the truth is he probably just wants to get up, shower, and head right out the door.

5) You’ll Feel Good About It

Finally, the biggest misconception about a one night stand is that you’re going to feel good about it. It’s simply not true. Yes, you will feel awesomely physically satisfied (hopefully), and you might even realize you’ve got your groove back now, but in a few days a little bit of doubt will enter your mind, or perhaps some cute old couple walking down the road will make you think maybe you want more, and one night stands will no longer satisfy you.

Dating a Co-Worker: Expectations

two young bussines people kissing in office

If you’re going to date a co-worker, you really have to tread carefully. First, many companies have strict policies against co-workers dating. Second, it’s never a pretty break-up.

1) Nobody Will Find Out

We always think we’ll be able to keep things on the down low, but the truth is people find out. Whether it’s the dreamy way you two look at each other, or if he says something, or you tell your best friend who in turn tells someone else, and so on and so forth… someone will definitely find out.

2) It’s Not Weird Seeing Him Around The Office

We expect it to be completely normal at work and all fireworks in the bedroom, but let’s face it: Can you really see him and not remember the way his mouth felt against your neck? Can you really look at him and not picture him naked? You can’t, which is why it’s definitely weird seeing him at work now.

3) You Will Sneak Off For a Quick Secret Kiss In The Lounge

Dating a co-worker often leaves us fantasizing about secret kisses or a quickie on the photocopier. Every time you see him walk by you’re tempted to pull him into the closet and rip his clothes off. However, the sad reality is that there will be no sneaking around at work. He will definitely be in work mode.

4) You Won’t Get In Trouble With Your Boss

If you’re at a company that has a “no dating your co-workers” policy, and your boss finds out, you could be fired. Actually, you both could be fired, so why risk it? The reality is that your boss isn’t going to care whether or not you’re in love, and your boss won’t think it’s cute and romantic, either. Your boss will find it a blatant disregard for the rules and you will be reprimanded.

5) If It Ends, You’ll Both Be Cool About It

Finally, the biggest expectation about dating a co-worker is that if it ends you will both be cool about it. This couldn’t be further from the truth. I dated a co-worker for six months once. When it ended, not only did he treat me badly around the office, but he also openly hit on my friends who didn’t know we had been dating. I actually had to quit that job because it was so uncomfortable.

One night stands can be spectacular. They can be a huge ego boost, an amazing sexual stress relief, and they can really make you feel good about yourself for a while. However, don’t expect your one night stand to come around again. If he does, and you end up having something wonderful, embrace it. Just don’t expect it. One night stands are meant to be one night only.

Also, dating a co-worker is almost never recommended. If you two like each other, then wait until one of you changes jobs or gets transferred to a different department or shift, where you never have to worry about bumping into each other.

About the author


Just another hard working mom who loves her kid, loves to write, can’t cook, and has a thing for tentacles! When I’m not hanging out with my Spawn, I’m happily sharing my dating experiences and offering advice and trying to control the chaos that comes with being human.

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  • Hi Trina, I love your article about the consequences of having a one-night stand with a coworker. What if you both never talked about it and work in different offices, but still have to communicate via chat or email for work? I am going back to the office soon where he works and just thinking about it makes me feel awkward. It’s been nearly a year since that night and we never talked about it. I’m not sure if it’s too late to even say something. We rarely have to interact now but I will see him everyday for a week in a few months. Should I just play it cool since it’s been almost a year?