How To Ask A Coworker Out On A Date

Getting into office romance can be tricky, and asking a coworker out on a date is trickier. You will continuously have to make sure to be as discreet as possible, not be too forward on the coworker yet express your feelings. Office romances and office dating are typical, it happens across all offices at one point or another. However, the person should keep in mind not to make things in office awkward. One should be polite and respectful when you ask a coworker out on a date. Also, the person should make sure to check on the employee associations as well as the official policies on office romance to avoid any issues later.

Ask A Coworker Out On A Date

Timing is everything! You cannot just ask the coworker out for drinks in the middle of work. Also, it is essential to check if the coworker is single or is already dating someone or committed. Checking on the single status would save time and embarrassment for both of you.

Looking for the Right Opportunity

You can do this by checking the social media handles of the coworker if the relationship status is mentioned there. Or you can ask any trusted coworker about the relationship status of the coworker you want to date, but be discreet. If none of this option works, then the only way is to ask the coworker yourself, treading the relationship status thing lightly just to get the information.

how to coworker out on a date


Dress Up Before Dating A Coworker

Be your best on that day, dress up well and be and feel confident about it. Relax in the morning, do any activity that would take the mind off stress or work up to about the ‘ask for a date’ thing. Wear an outfit that’ flattering yet suitable for the workplace. Be groomed so that you leave a good first impression. Brush your teeth thoroughly and use a mouthwash to keep any bad breath away.

dating worker

Dress Well While Ask A Coworker Out On A Date

Decide The Place Before Dating A Coworker

Approach the coworker in a comfortable place.  A right place is essential for both of you, and the coworker may not be pleased if you ask him/her for a date in the office room or the conference hall. Even if your coworker is interested in you, the right place will heighten the chances of agreeing for the date. Approach the coworker when he or she is alone. Don’t make the coworker uncomfortable by asking him or her in front of coworkers or other people. Make sure you have the full attention of your coworker and not ask for the date when he or she is rushing off to tend to something important task.

ask a coworker for drinks

Ask A Coworker Out On A Date for Drinks

The Date Proposal – How To Ask A Coworker Out

Be yourself when you are in front of the coworker; don’t feel nervous or shy. Don’t make the coworker further uncomfortable by being nervous. Remain calm and ask the coworker on a date. Asking for a date is the hardest part, though. You might feel nervous thinking about the aftermath or the response the coworker will give. It can be intimidating, thinking you will lose the coworker. But remember, you have nothing to lose. The worst thing that could happen is the coworker turning down the date proposal, and you excuse yourself out with a smile.

ask coworker out office romance

Ask A Coworker Out On A Date for Proposal

What to Say on the Date Proposal

Think and prepare what you will ask the coworker. Be casual and don’t beat around the bush and make the coworker confused and awkward. Vague talk is a huge turn-off. Make a small talk beforehand, keep it casual and then ask or the date. If you are not yet sure whether the coworker is interested in you or not, ask him or her for a movie date or a formal dinner to access their reaction. Instead of asking for vague places or saying things like ‘Do you want to go out with me?’, it is better to be clear about where you want to go and spend time together. This would make things clear for both of you and won’t be awkward too.

If you are conducting some social event, invite the coworker over there. If that feels forward, ask him or her to join you in some activity you are planning to do. Choose an appropriate activity or something for the coworker, like going to a concert or a festival. This way, the coworker will give a better response, and the chances of going out together when asked this way are naturally high.

Also, if you indulge in some small talk with the coworker, chances are he or she will end up asking your plans for the weekend.  After that, you can divulge your plan and ask the coworker to join you.

how to ask a coworker out

What To Say While Date With A Coworker

Friendly Vibe – How To Ask A Coworker Out

Create a familiar vibe with the coworker you want to date before asking for a date. This way, you both will develop a good rapport, and the interest from both sides may also build up until you ask for a date. This way, it will be convenient and much easier for you to ask the coworker on a date without being nervous or making them feel awkward. Keep the rapport and regular conversations casual and friendly so that none of you feels offended when eventually you ask him or her for a date. This method of asking the coworker out for a date works well if both of you have shared a great friendly vibe and make small talks regularly. Also, this method would be best if both of you are already flirting and are pleasantly interested in each other.

When you bring in the proposal for the date, let the subject come up naturally. Talk about a recent dating experience or dating scene in the office and pitch in your date proposal in the end. This is a tricky thing to do, and you should be good at analyzing the timings and execution. Also, this would not make the coworker feel awkward as the conversation would be on the same lines and who knows, he or she might end up responding with a ‘yes’ to your date proposal!

Make sure you are polite and not needy or rough when you ask for the date.  Get into a small talk conversation at first and then gradually ask about the date. Never rush things!

workplace romance

Ask A Coworker Out On A Date

How To Ask A Coworker Out & When it is a ‘No’ 

If the coworker turns down the date proposal, don’t get offended. Just leave it at that and never push repeatedly then or even later. Repeatedly asking a coworker for a date when the person is not interested is considered a hostile working environment and you’ll have to face the consequences in the end. If the coworker responds with a no, be polite and respectful and don’t hamper professional relations by pestering. The best thing to do is to excuse yourself and walk away.

how to ask coworker date

When To NO While Dating A Coworker Out On A Date

Whether Dating Coworker is a Good Idea?

Power Dynamic 

Always assess if dating is a good idea for both of you. Dating a manager, boss or senior at work will lead to undue favors at work, and dating a junior coworker would create a situation in an office where the coworker would feel pressured to hang out with you, and the relationship might get worse. Date someone who is at the same level professionally as you. This would ensure there is no power dynamic between you both.

Office Policies for Dating A Coworker

Always check the official policies on dating coworkers and office romance. Many organizations lay down specific rules, guidelines and even prohibitions on office romance and relationships. Check on the policies and guidelines before initiating the date or you both might end up losing the job. In organizations that have strict guidelines and rules on office romance, the relationship may get affected and also the productivity levels of both the partners may get changed, and both could get fired from the job. Check with HR regarding the policies. Also, even if the organization allows office romance and you get into one, avoid any forms of PDA’s, flirtation in office or giving preferential treatment to your partner at work. These activities at work will only hamper the professional careers and reputation of both.

Post a Break-up

Office relationships get wrong if the couple breaks up. The professional relationship between the partners’ posts a break up gets affected severely in an office. If both of you have to work o a similar project, then it is hell breaking loose! Ask yourself if you and your coworker would be collaborating efficiently at work in case of a break-up and then get into a relationship. If the answer is no, then it is better not to start dating at all! If the answer is yes, then you both should go for it.

Consider all options and situations that may occur after a break-up, this will help you to think about getting into a date first. Even if you and your coworker may not have to work together in a project, things can turn ugly and awkward in a workplace environment. You both will have to face each other at work, which might be uncomfortable for each other. This discomfort will be more if any one of the coworkers has feelings for the other. If you or your coworker feel awkward around each other at work after a break-up, then the performance levels at work may be hampered, and one of you might be obligated to leave the office in the end.

It is also essential to sit with the coworker and discuss what would happen if the boss comes to know about the office romance and asks anyone of you to end the relationship, or worse, leave the job. It is better to have a back-up plan and a response that both partners agree to.

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Jane Harper
Writer. Human resources expert and consultant. Follow @thehrdigest on Twitter

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