How to Ask a Co-worker Out on a Date?


You can’t stop thinking about one of your coworkers. Judging from the brief interactions you two have had at work, they seem like just your type. When away from the workplace, you’re constantly thinking of ways to ask them out, to get them in a one-on-one situation where you can get to know them better. Unfortunately, you’re finding it difficult to find the appropriate time or setting to make your move.

This is a common issue that many people face in professional workplace settings. Knowing what to say without sounding awkward and creepy during one of those brief moments of conversation can be paralyzing. However, here are a few suggestions that will not only pinpoint appropriate times to ask your coworker out but also allow you to create a smooth transition from work topics to getting to know one another better.

Ask Them to Lunch

Did YOU know?

1) Only 9 percent of women and 2 percent of men found a relationship at a bar or club

2) 38% of singles are using online dating

3) One in six marriages now begin online

People think they have to come up with some amazing pick-up line or be the smoothest person in the world to ask a coworker out at work, but this just isn’t the case. A simple but effective way to find some extended time alone with a co-worker is to ask them out to lunch. The casual nature that a lunch date presents alleviates some of the pressure that a first date might entail while providing that hour or so necessary to get to know him/her better. If the lunch goes well, don’t hesitate to suggest a future dinner or another lunch. The initial lunch date, while teetering on the line of whether it’s considered a date or not, allows you to get your foot in the door so to speak.

Set Up a Happy Hour Co-worker Gathering

Whether employees are sequestered throughout the entire day or supervisors and bosses are always present, some work environments simply don’t provide the opportunity to approach a coworker to ask them out on a date.

If that’s the case, then try to recruit coworkers to join you for happy hour after work one day. The goal is to create a relaxed environment where you relieve the tensions that many professional settings put on friendly and, in your case, flirty interactions. By removing yourselves from the workspace and creating a fun and light group setting, you feel free to openly engage in conversational topics that might otherwise feel inappropriate at work, not to mention the added benefit of introducing alcohol to the equation. However, a word of caution should be mentioned, don’t be that coworker who gets hammered and makes a fool of himself/herself. Be friendly and engaging, and when you’ve maneuvered your way into a conversation with him/her, be confident and make your move.

Plan a Group Outing

A great way to casually ask a coworker out is by inviting them to a group outing that you’ve set up with some friends. This can be a wine tasting, local festival, or cookout. Whatever it is, the dynamic of having others involved will alleviate the pressure that a one-on-one date would present. Your friends can help facilitate the ‘getting-to-know-you’ part while creating a friendly atmosphere that will allow you both to relax and have fun.

Cute But Subtle

The cute but subtle approach may seem a little corny to some, but if you feel a connection with a co-worker and there aren’t many opportunities to have a conversation where you could ask them out, try leaving a note wrapped around a piece of candy or chocolate that asks if they’d like to grab a cup of coffee sometime. This innocuous gesture comes off as friendly and cute and somewhat spontaneous, almost like you’re a kid again. It’s just a fun way to grab their attention without making a scene in front of others.

Coffee is the New Water Cooler

It’s no shock that most of your co-workers enjoy their coffee throughout a given workday, so it would be wise to find your way into the break room and strike up regular conversations with that person you want to ask out. You might not suggest going out the first conversation you have, but the more time you spend together in these brief moments of interaction the more comfortable you both become with each other. This will not only make is easier for you to ask them out, but they will be more likely to accept your proposal.

Get to know as much as you can in those short exchanges. Find out about things they enjoy doing, movies they most like to see, sports they prefer to watch, and then extend an invitation to something that connects with things they’re interested in.


Asking a coworker out can be an intimidating endeavor, but it doesn’t have to be. You don’t need to come up with some sleazy pick-up line to surprise them with. Stick to the suggestions given above, and when the appropriate time comes to ask them out, do so in a confident, yet lighthearted manner.