Considering that you spend most of your time at work, it makes sense that at some point, you’ll probably want to go out with someone that you met there and have gotten to know quite a bit. Still, the idea of asking out a coworker is still pretty terrifying. You don’t want to be too pushy, make things awkward at work, or come off as a creep, but you can’t shake off that giant crush you have on the guy who sits a few inches away from you. Here’s how to ask a guy out when you work together.
Take a good look at the situation.
Some companies have a strict policy against employees dating one another, so you need to check to see what the rules are in your workplace. The last thing you want is to put your career and his in jeopardy, so make sure you won’t be doing something wrong by asking him out. Is he your subordinate or superior? An unequal work status can potentially create problems for both of you. Consider how your office culture would be affected if people come to know you’re dating. If you date and break up, how awkward will things be?
Try establishing some sort of friendship first.
Don’t just surprise a guy you’ve never had any interaction with by asking him out on a date. He’s probably going to think you’re crazy and might not be open to the idea. Build a foundation by being friends with him. Find out whether you have anything in common besides mutual dislike for your manager or company. Learn things about him on neutral grounds and figure out if your personalities are compatible. If he seems genuinely excited or genuinely interested in your interactions, you can start building up the courage to ask him out.
Be polite and considerate when asking him.
There’s a thin line between asking a coworker out on a date and harassing them, and that line is your approach. You want to ask him out in a way that doesn’t make him feel uncomfortable. Avoid making sexual innuendos of any kind or behaving inappropriately. Don’t corner him or come on too strong. It’s better to approach him outside of work or in a communal setting like the lunch area. To reduce the tension, pressure, and awkwardness, don’t do it in the presence of other coworkers.
Act like yourself.
If you’ve worked with this guy for a while, he probably knows how you usually are, so now is not the right time to practice that new accent or completely reinvent yourself. It’s okay to be nervous, but try to keep it in check so you don’t scare him off. Stay calm and behave like you normally would and be respectful of boundaries at all times.
Be direct, but leave an easy way out.
If you’re vague when asking him out, he might misconstrue your intentions, or think you’re not serious, or that you’re just asking for a platonic hangout. You can ask what he’s doing this weekend. Then follow it with “I’d like to go to dinner with you, would you be interested?” This way he’ll know you’re asking him on a date, but he won’t feel pressured.
Pick a low commitment activity that’s safe for both of you.
Asking him to be your plus one to a wedding or buying tickets to a concert in another town would be classified as coming on too strong. There’ll be plenty of time for intense dates. Keep the first date light and breezy. Go with something simple like coffee, drinks, dinner, or lunch. Movies are okay, but they prevent you from actually talking and getting to know each other.
Be open to compromise.
He may not say yes right away because he’s actually got plans or doesn’t like the restaurant or date activity you suggested. If that’s the case, he may make a new suggestion for a different time or place. He might even want to take some time to think about it before agreeing to go on a date with you.
Know when to back off.
Don’t lose your cool if he declines to go on date with you. Just smile and say something polite to smooth over the situation like “No problem. Have a good weekend”. This is not a deal you’re trying to close, so don’t be pushy or keep asking him out until he agrees. If he says no, respect that and try not to take it personally. It could be that he has a strong personal policy against dating coworkers. Don’t hold a grudge. Don’t look for ways to get back at him. Just let it go. Not every crush is meant to be.
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