How To Ask Out A Coworker Without Being Creepy

Asking out a coworker can be a tricky situation, but can also be well worth it!

Asking out a coworker can be a tricky situation, but can also be well worth it!

You love your job (or at least the fact that it pays the bills), and understand that dating someone from the office could complicate things. Not only does asking someone out put you at risk for a sexual harassment claim, it could also make daily work life extremely uncomfortable when you have to see someone that turned you down.

But, what if Sally from accounting or Tom from sales is just too attractive to pass by any longer? If you’re okay with taking the risk, there is a methodology to asking out a co-worker. It’s not guaranteed to work, but it does minimize the chance of you getting fired, and is listed out in the steps below.

1. Get Socializing!

If you don’t already have a social relationship with the person you’re interested in at work, then it’s time to get social. Don’t start out by just going up to them and talking about yourself. Instead, talk to other people in your workplace and get to know them.

As you grow to know more people in your office, you’ll naturally come into contact with the person that you like. Once this happens, talk casually to them in a group setting, and keep the subjects neutral.

2. Get Out!

You need to get out of the office with your coworkers on a regular basis. For example, go out with a friend on your team for lunch one day, and regularly invite more and more people to come with you.

Gradually work your way up to happy hours or other social events that others are interested in. Converse during all of these outings, and be as social as you can while still getting to know other people.

3. Approach The Outings With Your Crush

So now that you’re more of a social butterfly at work, it’s time to talk to the person you’re interested in about the outings that you’ve been doing with co-workers. In order to do this properly, casually bring it up when you’re having a group conversation and they are around.

Ask them if they’ve been (this shows you’re not stalking them waiting for them to come), and why they haven’t attended. Mention that next time you have a group outing they should come, and leave it at that!

4. Time To Invite

This is the step that you have to follow carefully if you want to reduce your risk of things blowing up in your face.

Set up a group outing (say to a happy hour), and invite most of the usual people via work e-mail. Once you have about 6 people signed up, invite the person you like via e-mail as well.


For example, say “Hey Alex, a group of us are going out to a happy hour at Lou’s Tavern on Wed, you in?” This is the perfect invite, because if they complain to HR, you haven’t technically done anything wrong. And, if they say yes, you can anticipate seeing them outside of the office environment!

5. Enjoying The Outing

Once you’re out and the person that you like is there, make sure not to make things all about them. Talk as a group and still be social with other people, but try and include them in the conversation.

If you end up talking a little bit on your own, that’s a great thing! You’ll be able to use signs from them during your conversation to determine if a date is in the works, and then go from there.

Don’t rush things! If a few outings is required before you have the signs you need to ask them out on a future date, then wait! It’ll be worth it, and will put a lot less stress on your shoulders as well.

Most importantly, have fun!

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