Choosing the Right Opportunity
Determine if your coworker is single. Before you ever approach your coworker about going on a date, you should ensure that he or she is actually single. This can save you both a lot of time and embarrassment, and it can help keep your working relationship unaffected. If you're friends with your coworker, you can check his or her social media for hints of a significant other. Some social media platforms like Facebook have a designated profile line for relationship statuses. You can also browse through some of your coworker's recent photos to see if there are any pictures of your coworker holding hands or cuddling with someone else, which might indicate a relationship. If you have a trusted friend in the workplace, you can ask him or her about the coworker you're interested in. Ask your friend to be discreet, and just say something like, "I was thinking about asking _______ out on a date; do you know if he/she is single?" If none of these options are available to you, you could always ask your coworker himself or herself. Just tread lightly, and try to bring it up in conversation. For example, you might say something like, "That sounds like a fun plan for this weekend. Are you going with your boyfriend (or girlfriend) or friends, or just by yourself?" If your coworker is single, he or she might say something like, "No, I'm not seeing anyone. I'm just going by myself.
Look and feel your best that day. If you know your coworker is single and you've decided to ask him or her out, you should make sure you look your best and feel confident that day. Do something that morning that will either help you relax or get you psyched up, depending on your personality. You should also make sure you feel confident by dressing for success." Wear your most flattering outfit. Just make sure that outfit is appropriate for the workplace. Consider getting a haircut a few days before you decide to ask your coworker out. That way you'll look freshly-groomed and you'll make a good impression. Make sure you shower, and wear deodorant and clean clothes that day. Spend a little extra time grooming yourself so that your hair, facial hair (if you have any), and makeup (if you wear it) are perfect. Check your mouth in the mirror to make sure you don't have any food stuck between your teeth. Rinse with mouthwash or chew a mint shortly before you approach your coworker so that your breath is fresh and minty.
Approach your coworker in a comfortable place. Where and how you ask your coworker out are very important factors to consider. Even if your coworker is interested in you, he or she may have doubts or insecurities about approaching you, and so asking your coworker out in the wrong place, time, or context could create tension or even animosity. Approach your coworker when he or she is alone. If others are around, your coworker might feel uncomfortable or pressured into saying yes or no. Choose a comfortable space where you and your coworker will both feel safe. Don't ask your coworker out right outside the bathroom, for example, or in your office (if you have one), as these locations can be intimidating or even downright improper for asking someone out. A good place to ask might be a neutral work space, like by the copy machine in an office or when you're both behind the counter if you work in a restaurant. Make sure your coworker isn't rushing off to do something important, as you'll want his or her full attention for a moment when you ask.
Be yourself. As you chat with your coworker, it's important that you act like you normally would. If you're nervous, your coworker will notice it. And if you try to put on a fake persona, your coworker will definitely be aware of it and will most likely be turned off by it. Just remain calm and be respectful of your coworker at all times.
Ask your coworker out on a date. The hardest part is actually asking your coworker out on a date. It can be very intimidating, but remember that you ultimately don't have much to lose. The worst that could happen is your coworker may politely turn you down, in which case you'll just smile and politely excuse yourself. Be polite and warm when you ask. Don't come across as pushy or needy, and don't act disinterested. Make small talk for a few moments first, so it doesn't seem like you're rushing up to ask him/her out. Ask your coworker how he or she is doing, how his/her weekend was, or how his/her day is going. Transition smoothly into asking your coworker out. You might say something like, "Well hey, I really enjoyed talking to you. I'd like to chat more over coffee, if you're free this weekend?" If your coworker says yes, then say, "Great! When would be a good time?" If your coworker says no, be polite and cordial, but don't linger or make it awkward.
Know when to call it quits. If you've asked your coworker out and he or she is not interested, you'll need to leave it at that. Repeatedly asking a coworker out on a date who's already told you that he or she isn't interested in dating you could be considered a hostile work environment, which may end up getting you fired. Remember: if your coworker isn't interested in you, there are plenty of other people out there who would love to date you. Pestering your coworker if he/she isn't interested is not worth the time, effort, or the possibility of losing your job. If your coworker says no, be as polite and respectful as possible. Say something to defuse any tension, such as, "No problem. Well, I hope you have a good weekend." Excuse yourself and walk away. Lingering could make things awkward for both of you. Be polite and courteous to that coworker going forward, but make sure you never flirt with him/her or display any romantic interest now that you know he or she isn't interested.
Evaluating Whether Dating Is a Good Idea
Assess whether there is any type of power dynamic. The main situation in which dating a coworker is a bad idea (in fact, really the only reason at many places of employment) is if one of you is in a position of power. Dating your boss, manager, or supervisor could get you unfair favors at work. Similarly, dating your employee (if you're the manager) could potentially create a situation where your employee feels pressured to go out with you, and may be uncomfortable or unsafe breaking things off if the relationship isn't working. Only date someone you're at the same level with. As long as there is no power dynamic between the two of you, you should be able to safely date one another (as long as your place of employment allows it). Even if you are equals now, there is always a chance that one of you may get promoted in the future. That promotion, which is great for your career, could dramatically alter the nature of your relationship at work.
Determine your workplace policy on dating coworkers. Many places of employment have specific guidelines, rules, or even prohibitions regarding workplace relationships. Before you take things to the next level, it's important to know whether your employer will allow it, as you don't want to risk one or both of you losing your job. Some workplaces require you to disclose any intra-office romances to your supervisor. Others may have even stricter policies in place. You may need to describe the nature of your new relationship in writing, which may be difficult if you are both still figuring it out and haven't put any "labels" on it yet. Be aware that if your relationship has the potential to affect either of your productivity levels, you could both be fired from the company if the relationship makes your workplace behavior unprofessional. Check your employer's rule book (usually either given to you when you are hired or made available online). If you don't have such a rule book, ask someone who works in human resources or a similar position about any policies at your workplace. Remember that even if workplace romances are allowed, you may get into serious trouble for public displays of affection, flirtation in the workplace, using terms of endearment at work, or giving your partner preferential treatment.
Consider whether you and your coworker work closely. Even if you and your coworker are equals, there's still a risk of a bad professional relationship if things don't work out. If you're both able to be mature adults about it, then it should be fine. However, if you will have to work closely with one another, things could get complicated if you end up breaking up. Ask yourself honestly whether you and your coworker could continue collaborating at work if you recently broke up. A good way to gauge this is to think back to your most recent messy breakup. Could you and your ex sit at a table together and work on a project? If you don't think you could handle working with your coworker after a potential breakup, it may be best to avoid dating one another from the start. If you think you could both handle it maturely, then you should go for it and ask your coworker out.
Think about what might happen if it doesn't work out. Even if you don't have to collaborate or work closely, a messy breakup could still affect your workplace performance. Seeing one another at work everyday might be difficult, especially if one of you still has feelings for the other. This doesn't mean that things wouldn't necessarily work out if you and your coworker dated; rather, it just means that you should consider all possible outcomes before you proceed. Your performance levels may decline if one or both of you feel uncomfortable working around each other. One of you may end up feeling obligated to leave your department or the company altogether. If you're already friends with your coworker and are thinking about asking him/her out, you may want to have a serious chat with him/her about what you would both do if you were pressured by your boss to end the relationship. Have a backup plan in advance that you can both agree on.
Asking a Coworker Out in a Casual Way
Know what you're going to ask in advance. Don't try to wing it on the spot. If you approach your coworker, whether he/she is interested or on the fence, giving vague or ambiguous plans will likely be a turn off. Keep it casual, but know what you have in mind before you ask your coworker out. If you're not sure that your coworker is interested in you yet, asking him/her to something casual is more likely to succeed than asking him/her out to a formal dinner or movie date. Decide in advance what you'd like to do - for example, going out for coffee, or perhaps getting a drink together after work (if you're both old enough to drink). When you ask your coworker out, ask him/her out to whatever casual event you've planned. Instead of leading with something vague like "Do you want to go out with me?" you could instead say something like, "I'd really like to continue chatting over coffee or maybe a drink sometime, if you're free."
Invite your coworker to some social event you're going to do. If you're worried about coming across as too forward with your coworker, you can casually ask him or her about joining you at something you're already planning on doing. Just make sure you choose something appropriate to invite your coworker to, like seeing a concert or going to a street festival. The advantage of asking someone out this way is that it often comes up naturally in conversation. If you make small talk with your coworker, he or she will probably ask you what your plans are for the weekend at some point. This is the perfect opportunity to describe your plans, then invite your coworker. You might say something like, "I'm planning on checking out that concert this Saturday. I have an extra ticket - would you be interested in going with me?
Have a friendly "competition" over first date ideas. Having a friendly competition just means seeing who can come up with the best first date idea. This method of asking a coworker out would work best if you and your coworker already have a good rapport and make friendly small talk on a regular basis. The goal is, once again, to keep it casual and not make your coworker uncomfortable. This method will only work if you and your coworker are already flirting and it's clear that you're both interested in one another. Try to let the subject come up naturally. This can be a tricky move to pull, and the timing and execution need to be perfect or else it could sound creepy and off-putting. If someone in the workplace had mentioned having a disastrous date recently, you might say something like, "I feel bad for Shannon after that blind date. My ideal first date would be _______. What's yours?" Once your coworker responds with his or her ideal first date, you can say something like, "Wow, that actually sounds really fun. Would you maybe want to go sometime, for real?"
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