How to Ask a Coworker Out

When you work with someone, and you have a crush on that person, you’ve got a few things to do before you ask for that first date. Several risks come from dating at work, so there are several things to consider before taking the plunge.

Office romances happen, and in many cases, they can lead to happy relationships, sometimes to marriage. But, asking out a coworker in the wrong way can lead to severe problems like workplace harassment or sexual scandals. If you are dreaming of having an office relationship like Jim Halpert and Pam Beasley, learn how to ask a coworker out.

Considering that people spend eight hours or more at their workplaces, it is easy to understand why relationships develop. Most human resources experts do not recommend dating people at work, but when there is a connection, relationships happen.

Read Your Human Resources Manual

Before you approach the object of your affection, look at your human resources manual. Some offices have strict rules about office dating. Some businesses have limitations on who can date who and who should not have romantic entanglements. If you are in a position of authority, you certainly do not want to get involved with someone in a department you manage.

In some offices, asking someone can be a perfectly good cause for termination. You do not want to be the person who got your coworker fired. And you don’t want to get fired for asking someone out. You also do not want to be the reason why your business had to write a human resources manual and set rules for fraternization.

If your business does not have rules about coworkers dating each other, then you have to consider the climate of your workplace.

Do people hang out with each other after work? Are people in your office already married or dating? Does your workplace host social activities when people are off the clock? If your workplace is already socially open, then you shouldn’t have a problem asking out a colleague.

Understand Your Role at Work

The best office relationships happen when partners are on equal footing. For example, it is common for two teachers to have a relaxed relationship at work because they have similar statuses at work. Even if one has more seniority, neither is in a position of authority over the other. Problems might happen if a principal started to date a teacher, due to authority issues.

If you idolize Jim and Pam’s relationships, remember that they were equals at work. Jim was in sales, and Pam was a receptionist, but she eventually moved to sales. Neither was the other’s boss, except for the short time when Jim was in charge. Once he took on a leadership role, the rest of the office questioned his motives when he rewarded his employees, and Pam won.

Bosses aren’t the only ones who can have problems if they date someone they supervise. The person in the lower department can also have problems. No one wants to be blamed for using romantic relationships as a tool for promotions. Even though people love who they love, workplace roles can create problems with workplace relationships.

The general rule is not to date anyone who has control over your career or anyone whose job you control. Neither situation will end well, for anyone. Underlings become alienated, and supervisors lose their authority.

Consider Your Coworker’s Life Outside of Work

Before you ask out your coworker, you should learn a little about him or her. If you only see your coworker at work, you are missing out on seeing your coworker in the real world. Some people behave differently at work than they do at home or socially. Your coworker might already be in a relationship or live a life that does not interest you.

While you shouldn’t spy on your coworker, it is your best interest to learn what you can about your colleague. You don’t want to be embarrassed by an awkward rejection. You also don’t want to be uncomfortable at work if things don’t go well. You also don’t want to be accused of anything that could taint your reputation professionally and socially.

Remember that no matter what you do or don’t do, you still have to go to work each day. Asking someone out at work can create problems that you’ll have to face daily. Get to know the person before you do something that you cannot take back.

Instead of spying on your coworker, find someone who knows your crush well and ask a few questions. Sometimes, mutual colleagues can be the most helpful advocates of dating in the workplace. Hopefully, the friend will let you know if your coworker is available.

Don’t ask your colleague to communicate for you, though. Only you can ask the coworker out. If you are worried that your mutual friend might create a problem, be discrete about the questions you ask. Otherwise, your mutual friend might crush your plans.

Contemplate if You Work Closely

Some employees work together more than others. If things go well, work could become fun. But, if things do not go well, how often will you see each other? When you work in the same department or if you might have joint projects, the discomfort level could skyrocket.

There are several reasons why some people will never date a coworker. One of those reasons is the possibility of an ugly breakup. It can be difficult for people to see each other after breaking up. Consider how difficult it would be to work with someone who broke your heart, or vice versa.

If there is no way that you could be comfortable with these situations, then you probably shouldn’t date a colleague. If you are ok with it, then it’s worth a try.

Consider Your Coworkers

If you do decide to ask out a colleague, you will eventually have to work together. And your other colleagues will ultimately learn about the event. If the relationship begins to develop, you will want to consider how you will interact at work. You shouldn’t show off your relationship, as it can become problematic for the rest of the office. No one wants to see PDA or flirting.

You should also consider how you will interact at work so you can still get your job done. Your inside jokes should remain outside of the workplace. You do not want to give your colleagues any reasons to complain about your relationship. You don’t want your relationship to affect the way business gets done.

It is also essential to consider your colleagues if the relationship does not work out. There could be some awkward moments between the two of you, and your colleagues might feel uncomfortable around you both. Again, you do not want to create reasons that people complain about your interactions with colleagues.

If asking out a coworker will affect your productivity at work, then you probably shouldn’t do it. But, if a relationship starts to happen, you should talk to your boss or the human resources manager. Explain the situation before anything gets out of your control. Your boss will appreciate you saying something rather than being blindsided by a complaining colleague.

How Many Times Do You Ask a Coworker Out

The short answer is one. If you must ask out a coworker, you shouldn’t try several times. When a coworker says no, that’s it. While persistence is useful in some circumstances, it is not wise to be persistent in this situation. Failing to accept a no answer can result in harassment complaints that could force your boss to fire you.

If you do ask out a colleague and the response is something other than yes, you should take that as a no. Some people are uncomfortable with declining an offer. Instead, they might say they are busy, or they have other plans. Unless you get a certain yes, every other answer is a no. Do not cross the line and ask out your colleague a second time.

It doesn’t matter if you are a man or a woman when you get a no answer, you stop asking. You do not want to make someone feel uncomfortable at work. Respect the answer and move on with your life.

When businesses set dating rules, the limits balance power between the asker and the answerer. Managers at Facebook have revamped their dating rules, enacting the one-ask rule. Google also has a dating code of conduct that could result in dating employees being transferred to different departments or being let go.

Try Friendship First

Before you take the big step of asking someone out, you should take time to develop a friendship first. Pam and Jim were friends long before they ever dated. All the while, Jim had a crush on the endearing receptionist. If they hadn’t become friends first, the iconic modern relationship would not have evolved the way it did.

When you become friends with a colleague, you can go out in a pair or with a group. You can talk about work and about your lives outside of work. Friendships tend to be safe, as no one has control and going out as friends does not have the same awkwardness as dating can. Friendships do not have the same risks that romantic relationships have.

With a friendship, you get to know your coworker socially. You get to find out if you actually do want to date the person, or if a friendship or professional relationship will be enough. With a friendship, you have time to decide what to do. And you do not have to worry about being awkwardly rejected.

In most workplaces, friendships are perfectly acceptable. When you are friends with people at work, the workplace is happier. But, if you prematurely ask someone out and you are rejected, the workplace becomes uncomfortable. Friendship just might be a way to go, especially if you want to have fun at work and not worry about being nervous and out of control.

Consider Your Past Relationships

Before you attempt to bring romance into the workplace, consider how you are feeling. Have you ever had a workplace relationship? If so, how did it go? Were you recently in a relationship? Are you acting prematurely? How did your previous relationship end? How long did it take you to recover?

Workplace romances can be complicated. They can also be wonderful. Sometimes they end so badly that the two parties look for work elsewhere. If you’ve tried the office relationship before and it didn’t work out, you might not want to try it again. People who have dramatic endings to relationships should avoid workplace romances, as they aren’t bound to end well.

Drama-filled workplaces might be fun to watch on television, but they are not fun places to work, especially for the people involved in the drama. Before you put yourself out there, you should take a good look at yourself and how you act and react in romantic relationships. Do you really want your colleagues to get to know you that way?

Where to Start

After you’ve done your research and made sure that you won’t get fired for asking out a coworker, start with something simple. Instead of asking to go out on a date, ask your colleague if they would like to get coffee. It’s a low-stress question that is easy to answer. Coffee shops are casual and relaxed, so the location isn’t as intimidating as a bar or fancy restaurant could be.

Asking to get coffee is something that friends do together. Getting coffee is usually not perceived as being romantic. It’s a nice place to sit, drink coffee, and chat. Asking to get coffee is a safer question than asking to get dinner or drinks.

When you ask your coworker to get coffee, suggest meeting for coffee. This way, there is no discomfort about how to get there. Meeting for coffee also takes away any awkwardness that could happen after the event is completed. You don’t have to worry about kissing or anything else. You are merely meeting for coffee. Even the dress code is easy.

If the coffee shop isn’t going to work, you could try asking your colleague to join you at a fun social event. You can do this in the middle of a conversation. For example, if you are talking about the food you love at an upcoming local festival, ask your coworker to join you to try your favorite dish.

Another idea is to start a conversation that ends up with your coworker as you about your weekend plans. After they ask what you are doing, tell them, then ask them to join you at the ball game because you just so happen to have an extra ticket.

Don’t wing it. Have a few plans so you can ask the question when the opportunity arises. Be light and breezy, so you don’t come off as a creeper. It is always best to ask the question in the middle or end of a conversation. If you are having a good chat, offer to continue it later at a coffee shop.

Avoid Being Awkward

When a coworker asks out another one, the way the question is asked should be planned. Unfortunately, a common sexual-harassment complaint isn’t that a colleague asked out another one, but how the asking out went. When the question comes off awkwardly and uncomfortably, things can go very wrong – sexual-harassment-claim wrong.

If you are worried about asking awkwardly, take time to practice with a friend. Be aware of your body language, vocal tone, and word choice. You do not want to come off as intimidating or as a creeper. You want to be relaxed and light in the way you ask the question.

Do not ask the question in private, because that can be intimidating. Ask your question in a public area, or outside of work. When you ask the question, offer an out. For example, you could ask if they would like to get coffee, but if they’re busy, it’s ok. This shows that you aren’t creepy and that you understand your colleague has a life outside of work. It’s respectful.

Be Prepared for Yes and No

No matter what your colleague says, you still have to go to work together. So, if your crush says no, you have to stay calm and accept the answer while remaining light and relaxed. The worst thing you can do is get mad or ask again. So, have a response ready for a no answer. The best thing to do is to change the subject, chat for a brief moment, then continue on your way.

If your colleague says no, remember not to take it personally. Some people will not date people they work with, and some people are just busy. If your colleague says they are busy, you could always say, maybe some other time. Then, let them approach you with the question. If they clearly say no, then you never ask again.

On the flip side, if you get a yes answer, you still have to stay professional. You might feel like doing cartwheels, but you can’t. You are going to have to work together, and you never know how the date will go. Your workplace dynamic could change, even if you get along well. Your relationship could be life-long, or it might end in an ugly way.

No matter what answer you get, keep this policy in mind: do not contaminate the workplace with your relationship.

Ask in Person

When you ask out the person, only do it in person. You might be tempted to send an email or text message, but don’t. When you ask the question in person, it shows that you respect the person. Sending a text indicates that you are fearful; it just doesn’t look right.

On the day that you ask the question, be sure that you look nice. You are more likely to get a yes answer if you look your best. Make sure your hair looks good and that you smell fresh – especially your breath. Check out your teeth to be sure you don’t have food stuck in it. Don’t forget to smile, but not in a creepy way.

If you aren’t sure what to wear, pick something appropriate for work and comfortable for you. It is also wise to avoid wearing something that you fidget with, too. For example, if you can’t keep your hands off of your tie when you are nervous, do not wear one when you ask out your coworker.

Pick the Right Time and Place

When you ask is almost as important as how you ask. If your colleague is in the middle of something or making a beeline to the restroom, then wait until a better time arises. When your colleague is busy, you can expect a no answer. But, if your colleague is in a relaxed space, not focusing on something intense, you are more likely to get the yes.

When you pick the right time, make sure you have the right place, too. The communal places at work are ideal because other people are around, and your coworker will feel safe.

This doesn’t mean that you should ask out your coworker in front of a bunch of people because you shouldn’t. But, you should ask out your colleague in a public space, rather than in a private office. The key is to pick a comfortable place and not a place where your coworker will feel trapped.

Pick a Topic for Conversation

Before you ask the question, you should take time for small talk with your coworker first. Consider how awkward it would be if you just walked up to your colleague and ask about going on a date. Your coworker won’t have time to relax into the conversation. Instead, start the moment with a discussion about something you have in common.

Hopefully, this isn’t the first time that you’ve talked to your coworker. Before the ask-out moment, you should know something about the person, like their favorite shows or music. Maybe you can talk about vacations, cars, pets, or food. Pick something easy and comfortable; don’t talk about work, politics, or religion.

The Date Went Well. Now What?

If all goes well, you have some work to do. You will have to set some ground rules, so you don’t get in trouble at work. You might have to talk to your human resources manager to share that you are in a relationship. Ideally, no one should be able to tell you are dating. If they can, then you are doing something wrong.

It is also a good idea to go slow. Take time to get to know each other before you become romantic or intimate. You will have to work together, even if your relationship ends. The slow factor should also include not announcing your relationship to your colleagues until it has become something officially serious.

When at work, you should focus on work, not on each other. If you are working on a project together, do not flirt with each other or show any public displays of affection. Don’t grab at each other under the table, or over the table.

You must maintain your professional relationships with your colleagues. Often, those grow at lunches or informal conversations. Do not give up on those relationships, just because you are dating someone in the office. Have lunch with your colleagues, don’t shut yourself off from them by only spending time with your significant other.

Keep in mind that you could become a subject of gossip. When your colleagues start talking about you, the word could get your boss. If your boss finds out, you could have trouble managing. In some cases, you could even end up with sexual harassment accusations. If you are showing PDA at work, expect someone to complain.

Along with avoiding PDA at work, you should also avoid private ones. The chance that someone could see you is reason enough to avoid trying to sneak a kiss at work. This also goes for sexy emails. When you are on work computers, your boss expects you to be professional. If you send flirtatious emails or inappropriate photos, you could get fired for misusing company technology.

You will also want to set ground rules for your dates. Many couples who work together decide not to discuss work when they are on a date. You don’t want colleagues to gossip about you, so you shouldn’t gossip about them. Talking about work can ruin a romantic moment, which is why you should set rules about talking about your workplace.

You should also take time to talk about what happens if things work or if they don’t. The future conversation shouldn’t happen until you are both aware that there is a future. Then, be serious and decide what will be best for you professionally and personally.

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