10 Questions To Ask Before Sleeping With Someone From Work

With Christmas party season incoming, here are all of our best work affair war stories to prepare you for that 'just one drink on the way home' with your colleagues. Eye roll...

Should I sleep with my work colleague?

by Georgia Aspinall |
Updated on

It's that time of year again. The drinking is starting, the work Christmas party is on the horizon and all the single people are regretting not cuffing someone earlier in the season to secure that all-important Christmas present. Alas, office romances are bound to happen during the numerous pub visits and liquid lunches we're all beginning. But is it ever wise to sleep with a colleague?

We've got the war stories, and the psychological expertise of Counselling Directory member Philip Karahassan, to find out what you should be asking yourself before plunging into an office affair...

1. What's the work protocol?

‘In the moment, stopping to consider what your employer may think is probably the furthest thing from your mind,’ says psychologist Philip Karahassan, ’however, different companies have different protocols around romance at work, so make sure you know if work with deal with it should they find out. Remember, it might be fun in the moment but that moment could have further repercussions for your career.’

'My last employer had a no-dating policy at work, but no one followed it,' says Emma, 24*, 'when he finally clocked that everyone was secretly at it, he held a really awkward meeting explaining the "anti-fraternization policy", then ended up calling everyone into HR meetings over the next few weeks who were quite clearly in full-blown relationships. It was weird, but it definitely put me off starting any office romances, just to save the awkward meeting.'

2. What if you get the office STI?

‘I slept with a guy from work who ended up giving me an STI,’ says Anna*, 28, ‘but I didn’t realise he was also sleeping with another colleague, and so on one of our work night outs I told one our mutual friends in the office about it, and she then had to go tell the other woman he was sleeping with that he was sleeping with me too, and she likely had the same STI. Slightly awkward’

3. How do you feel about each other?

‘It is important to understand if this will be a one-night stand, or if you are expecting something more,’ says Phillip ‘Make sure that both of your feelings match up, otherwise there may be expectations of something more after your night together and that those feelings might not be reciprocated, which could make things quite tense in the office.’

'I invited a bunch of work colleagues to my birthday and ended up back at mine with this guy that hadn't been there long,' says Sophie*, 23, 'I thought it was just a bit of fun, since we'd literally had like four conversations, but he started texting me incessantly afterwards about how he'd fancied me since he started and couldn't wait to take me out.

'I'm typically a full ghoster when I don't like someone, so having the 'i'm not interested' chat was horrendous,' she continues, 'but the worst moment was the week after when we were both heating up food in the kitchen at the same time and just stood in silence watching the microwaves. It was the longest 90 seconds of my life.'

4. Do they have a common name? It might cause some confusion…

‘I slept with my boss whose name was Dan, but there were like five other Dan’s that worked there,’ says Anna, ‘so one day my colleague was gossiping about it all and started telling my boss assuming it was a different Dan. He literally had to say to her “actually it’s me not the other Dan” because she wouldn’t stop talking about it, her face was a picture.’

5. Have they slept with anyone else in the office?

‘I totally had my head turned by an average looking, but quite charismatic guy in the first proper office I worked in after uni,’ says Daisy*, 34, ‘I knew he’d had a bit of a thing with one of the other women who worked there, but that seemed to be over. After a couple of months of vague flirting, but only when he’d had a LOT to drink - another warning sign - we finally got it on at a work party.

'He totally ignored me afterwards, which I would have been fine with, were it not for the fact that A, everyone, literally everyone in the office knew what had happened and B, he’d already slept with seven other women in the office. For context, there were 29 people in the company in total.’

6. Have they been honest about their relationships outside of work?

‘After a work Christmas party, I was caught snogging a guy I worked with in the corridor next to the disabled loos by HR and warned about getting “carried away”,’ says Jennifer*, 34, ‘we had a very awkward, hungover lunchtime conversation the next day, where he admitted to me that the girl he was seeing was his live-in partner of ten years, who was very keen to get married. Apparently, all the pressure she was putting him under was making him “act out.” Poor thing (this is sarcasm)'.

7. What if everyone in the office finds out?

‘Everyone I used to work with knows about the couple who were having an affair, and who were both randomly found in the office together at the weekend by someone who’d come in to do their expenses,’ says Daisy, ‘It was incredibly obvious that they’d taken the opportunity to have sex on the CEO’s desk, and everyone in the office knew about it by 10AM on Monday. Which was pretty speedy in the days before WhatsApp.’

8. What if your secret rendez-vous follows you to another job?

'I used to work in a ski resort as a rep, literally everyone is shagging and there are always STI's flying about,' says Ella*, 24, 'this one company I was working for was known for the STI all the staff got one year. Seasonal work is really incestous in terms of who you work for, so when I started working festivals in the Summer a few of the same people were there, and the rumours were still flying about this one guy who'd started the STI spread. I don't think he escaped it until he moved industries, to be honest.'

9. What if the sex is bad?

'I went on a work night out once and went home with one of the new guys, he had a good body but I didn't fancy him that much so when it came to doing the deed I wasn't really turned on enough to get going,' says Emily*, 25, 'instead of him trying to turn me on, he just got really huffy shouting "this never happens to me" and stormed off. Like, was he expecting waterfalls just from looking at me? It got really awkward really quickly so I got away as soon as possible.

'Nice guy that he was he made this really, really uncomfortable at work after that, I didn't last there much longer there.'

10. Do you feel safe?

‘Alcohol consumption definitely increases during the festive season, so make sure both you and your colleague are fully in control and able to give verbal consent before doing the deed,’ says Phillip, ‘This is not only a good question to ask before sleeping with someone you work with, but something to always keep in mind.

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