Asking a coworker out on a date is a tricky business. You don't want to be too direct, but you want to show interest. You also don't want the work environment to be awkward, but the urge to be with him may already be excruciating. In fact, peer-to-peer relationships are commonplace and generally acceptable. If you ask her out in a polite and respectful manner, and as long as both parties can maintain professionalism in the working relationship, there's nothing to worry about. However, it's a good idea to check the employee manual or check with the HR department about workplace romance policies so you can avoid problems along the way.
Step
Part 1 of 3: Choosing the Right Opportunity
Step 1. Make sure that he is single
Before making an approach, you should know for sure that he is still single. That way, you won't be wasting time and can avoid embarrassment, and make sure the working relationship isn't affected.
- If you're already friends with her, check her social media for clues to where other people are in her life.
- Some social media platforms such as Facebook provide special descriptions for relationship status. You can also browse recent photos to see if there are photos of him holding hands or embracing with the opposite sex that indicate a romantic relationship.
- Ask a trusted friend at work. Ask him to keep it a secret, and say, "I want to ask Rini out on a date, do you think she's still single?"
- If neither option is available, you can always ask the person in question directly. Insert light questions about his status in the conversation.
- For example, "Looks like plans for the weekend are going to be fun. Do you want to come with your boyfriend or by yourself?" If he's single, he might say, "No, I don't have a boyfriend. I came alone."
Step 2. Make sure you look and feel great for the day
If you know he's single and decide to approach him, you need to look good and feel confident. In the morning, do something that will help you relax or mentally prepare, depending on what works best for you. Also make sure you feel confident by choosing clothes carefully.
- Wear clothes that show the most appeal. Make sure the clothes you choose are suitable for work.
- Consider getting your hair cut a few days in advance. Thus, you will look fresh and able to make a good impression.
- Make sure to shower, and wear deodorant and clean clothes. Prepare your appearance carefully so that your hair, beard or mustache (if you have one and you're a boy), and make-up (if you're a girl) are perfect.
- Check the inside of the mouth in the mirror to make sure that there is no food debris stuck to the teeth. Clean your mouth with mouthwash or eat mint candy before approaching it so that your breath is fresh and smells good.
Step 3. Approach him in a comfortable place
Where and how to ask out on a date is very important to consider. Even though he's also attracted to you, he may be doubtful or insecure. So asking out on a date in the wrong place, time, or context can create tension or even displeasure.
- Approach him alone. If someone else is nearby, she may be uncomfortable or feel pressured to answer immediately.
- Choose a comfortable place where you both feel safe. Don't approach her outside of your bathroom or room (if you have your own room) because that location creates the impression of being intimidating or inappropriate for a date.
- A good place is a neutral workspace, such as the coffee photo area in the office or behind the counter if you both work in a restaurant.
- Make sure he's not in a rush, because you'll want him to give your full attention to the moment you ask him out.
Step 4. Be yourself
When chatting with him, you should act normal. If you are nervous, he will notice. And if you present yourself as someone else, he's bound to notice it and will likely change his mind. So you should always be calm and respect him.
Step 5. Ask her out on a date
The hardest part is getting the word out. It can be scary, but remember that you have nothing to lose. The worst risk is simply being politely rejected, and in that case you just have to smile and excuse yourself politely too.
- Invite him nicely and warmly. Don't come across as urgent or desperate, and act like you're not interested.
- Start with small talk so you don't sound rushed. Ask him how he was, how was the weekend, or how was his day.
- Seamlessly turn chats into invitations for a date. You could say, "It's been fun chatting with you. I'd like to chat again, maybe over coffee, if you're free this weekend?"
- If he says yes, say, "Good! What time should it be?" If he says no, you should respond in a polite and friendly manner, but don't linger or make the situation awkward.
Step 6. Know when to stop
If he's not interested in your date, it's best to just let it be. Repeated invitations to dates when he refuses can be seen as disturbing the comfort of work, which could get you fired. Remember, if he's not interested, there are plenty of other people who would be happy to date you. Annoying an uninterested coworker is a waste of time, or worse, you lose your job.
- If he refuses, respond politely and respectfully.
- Say something stress-reducing, like, "It's okay. Have a nice weekend."
- Excuse yourself and walk away. Hanging out after being rejected will only create awkwardness for both of you.
- You should still be polite to him, but never flirt with him or show any romantic interest after you know he's not.
Part 2 of 3: Evaluating Whether Dating Is a Good Idea
Step 1. Assess whether there is some kind of power dynamic
The main problem that makes dating between coworkers a bad idea (in fact the only reason in many workplaces) is when one is in a position of power. Dating your boss, manager, or supervisor can bring you an unfair advantage. Likewise, dating an employee (if you're the manager) has the potential to create pressure for him to accept your date, and make him uncomfortable or insecure about breaking up a relationship that isn't working.
- Make sure you date coworkers who are on the same level. As long as there is no power dynamic, you can be in a relationship (if permitted by company policy).
- Even though they are currently equal, there is always a chance of one getting a promotion in the future. These promotions are great for a career, but can have a drastic effect on relationships at work.
Step 2. Determine how the company policy regarding the relationship between employees
Many companies have guidelines, rules, or restrictions regarding workplace relationships. Before taking your coworker attraction to the next level, make sure that the company allows it because you don't want to lose your job.
- There are some places that require employees to notify supervisors of relationships in the office. Other places may have stricter policies.
- You may be asked to describe your relationship status in writing, which can be difficult if the relationship is raw and doesn't have a "definite status" yet.
- Realize that both of you could be fired from the company if the relationship has the potential to affect productivity and reduce professional behavior in the workplace.
- Check the company rulebook (which is usually given when you are hired or available online). If you don't have a rulebook, ask a person in the HR department or similar position about workplace policies.
- Remember that even if a relationship at work is allowed, you can still get into serious trouble if you show affection, flirt, use affectionate words, or pay special attention to your partner at work.
Step 3. Consider whether you and he are working together
Even if you and he are on an equal footing, there is a risk that the professional relationship will deteriorate if the relationship doesn't work out. If both parties are able to act maturely, there is no problem. However, if the two of you have to work together, things can get complicated if the relationship ends.
- Ask yourself and honestly answer whether you and he can still collaborate if the relationship ends.
- A good way to measure it is to think about your last breakup. Can you and your ex sit down together and work on a project?
- If you feel like you can't work with your ex, it might be best to avoid dating coworkers in the first place.
- If it seems like you and he can overcome relationship failures as adults, then try and ask him out on a date.
Step 4. Think about what might happen if the relationship doesn't work out
Even if you don't need to collaborate or work together, a messy breakup can still affect work performance. Meeting in the office every day may be difficult, especially if one is still harboring feelings. This does not mean relationships with coworkers will not work, but just as a consideration before taking a step.
- Performance may decrease if one or both parties feel uncomfortable working together.
- One may feel obligated to leave the department or even the company.
- If you're already friends with her and are thinking about asking her out, consider having a serious conversation about what to do if your boss pressures you to end the relationship. Have a mutually agreed backup plan.
Part 3 of 3: Invite a Casual Date
Step 1. Prepare what you want to say
Don't think about words as you go. Vague or ambiguous plans will make him lose interest, whether he's interested or hesitant at first. Ask casually, but prepare your words first.
- If you're not sure if he's interested, a casual invitation is more likely to work than an invitation to a formal dinner or a movie.
- Decide what you want to do on the date, like drink coffee.
- Invite him to do the relaxing activities you have planned.
- Instead of asking, "You want to go out with me?" it's better to say, "I'd like to chat again over coffee or a drink, if you have time."
Step 2. Invite him to a social event you will attend
If you don't want to be too blunt about asking her out, ask her to join you at an event you're going to. Choose an appropriate event to invite her to, such as a concert or a street festival.
- The advantage of an invitation like this is that it seems natural if tucked into ordinary conversation.
- During small talk, he may ask what your plans are for the weekend. This question is the perfect opportunity to describe your plans and then invite him or her to come along.
- You could say, "I'm planning on going to a concert this Saturday. I have an extra ticket, would you like to go with me?"
Step 3. Choose a date idea through a fun "competition"
The fun competition is just to see who has the best first date idea. This method works best if you and the other person are already friends and chat often. Again, the goal is to create a relaxed atmosphere and make him comfortable.
- This method will only work if you and he are already flirting with each other and there is a clear interest between the two of you.
- Try to bring up the topic of dating naturally. This approach will be difficult, and requires perfect timing and execution because if you don't take it into account, he will get scared and lose interest.
- If another coworker recently told you about a failed date, you could say, "Poor Sari, he went on a blind date yesterday. The ideal first date for me would be _. How about you?"
- After he responds with his own dream, you can say, "Wow, that looks like fun. Do you want to give it a try, for a real date?"
Tips
- Know the company's policies on workplace romance, and adhere to them. Know if you should disclose the relationship, and if so, to whom.
- Usually, it's better to keep the relationship a secret than to tell your boss, supervisor, or HR person (if company policy requires it). Do not show affection because it will make other colleagues uncomfortable.
- Maintain professionalism at work. This doesn't mean ignoring him or pretending you don't know each other, but don't hold hands, kiss, or show affection.
Warning
- A business meeting or meeting does not include a date. Keep business communications and personal communications separate.
- Don't use corporate email to send love messages. If your email is monitored or its contents are discovered, you could be fired. E-mails containing a date to a co-worker can also potentially be used as evidence against you in a sexual harassment case.
- If your relationship makes other colleagues uncomfortable, they may complain to management. While romance at work isn't against policy, you should always act professional in the office. Better to play safe than sorry.
- If you misinterpret the "signal" or behave inappropriately, you could be sued for sexual harassment.
