Ask A Straight Guy: How Do I Ask Out My Office Crush?

How do I ask out my office crush

The reaction to last month’s #AskAStraightGuy dating column was so great that we’ve invited Oli back to help solve more reader dilemmas. Jennifer* got in touch shortly after the first post went live to seek an outside opinion on her current romantic conundrum. It’s a tricky issue – “How do I ask out my office crush without making things awkward?” – and here’s what Oli had to say…

THE DILEMA: “I’ve always been against dating in the workplace, but last November a new guy arrived in the office and I developed a massive, uncontrollable crush immediately. I thought it would pass, but over the last few months we’ve spent a lot of time working together and my feelings have only intensified.”

“We have a very flirtatious relationship and a lot of our co-workers tease me about it. However, I’m not sure if he realises I have serious feelings for him and that the flirtation isn’t just playful office banter. I feel too embarrassed to ask him out in case he doesn’t feel the same way and it makes things awkward. Is there anything I can do to show that I’d be receptive to him making the first move?”

OLI’S ADVISE: “I have so many friends and clients who over the years have said to me, ‘I met someone lovely but didn’t ask them out because I was worried they’d say no.’ I think that’s such a shame, and this embarrassment stigma shouldn’t even exist. But, at the end of the day, it’s better to suffer a little embarrassment than miss out on being with the raddest person in the world.”

“I can understand how it could feel awkward, but there’s no smoke without fire. You don’t flirt with someone every day unless there’s a certain level of chemistry or attraction there. So there’s a strong chance he is interested in you. A lot of girls assume, ‘He doesn’t like me because he hasn’t made the first move’, but I know loads of guys who are terrified of asking women out. And I also know a lot of couples who are only together because the girl made the first move.”

“Just say to him, ‘Oh my God, it’s been a long day! Do you want to grab a quick drink?’ Or, if that feels to bold, instigate drinks with a group of people, see if he’s flirty outside the office and then suggest the two of you get drinks together later in the week. If he says yes it was worth the gamble, and if he says no you’ll stop hypothesising about what could be. You have to give it a shot!”


Oli The Elgin Avenue 2

ABOUT OLI: Oli has been in a relationship with Monica Welburn from The Elgin Avenue for 7 years, and can always be relied upon to give practical, no-nonsense advice. As a hairdresser he spends most of his days counselling male and female clients through their relationship woes, so by now has heard it all.


If you would like some straight-talking advice from Oli you can submit a dating dilemma to cocosteaparty@gmail.com (please put #AskAStraightGuy in the subject line). We can of course keep identities a secret. 

P.S. #AskAStraightGuy: Am I texting my crush too often?

* Names have been changed

  • sounds like good advice, the embarrassment will eventually fade but regret can linger for some time. can there be follow ups to these posts, i’m curious to know how they go 😉

    • cocos_tea_party

      OMG that would be amazing. Will have to look into that and see how it could work

  • One thing I’d consider is whether office relationships are ‘allowed’ at your place of work. Not all employers look kindly on them, as if they go wrong things can get awkward, fast!

    Becky | accoohtrements life, travel & design blog

    p.s. I met my boyfriend at work and we still work together 3 years later! I nearly sweated to death when I told my boss we’d got together but she said “Oh I met my husband here!”!

    • cocos_tea_party

      Can’t believe I’m only just replying to this comment, but totally agree about checking it’s “allowed” first. And that’s so lovely to hear about you and your boyfriend. Do you still work together?

  • Alice

    I met a (now-ex) boyfriend at work… I just said I was having a crappy day, he suggested drinking gin in his office that afternoon, and then three glasses in, he kissed me. Perhaps not the most usual way to start a workplace romance, but it was great fun!! (And has been remarkably un-awkward since we broke up- but then, we never worked closely together… I’d say that it’s worth proceeding with caution if you do!)