I have a coworker who I'm kind of into and I think she might be into me. How do I clearly express this without making things awkward at work if she says "no", or if she says yes, for that matter? Is that even realistically possible? Thanks.
Are you sure you want to get "involved" with a co-worker, if it ends badly you still have to see them. Trust me been there done that and it can get pretty ugly and makes for a stressful work environment for other co-workers as well.
No one can make you jealous, angry, vengeful, or greedy -unless you let him.
- Napoleon Hill
My immediate advice is: Proceed with Caution
I don't know where you work, so I'm uncertain as to the dynamics involved in coworker dating. If you both work in a retail store or the movie theatre or a restaurant, coworker-relationships probably aren't as prone to potential long-term disasters than if you both work in a cubicle-zoned corporation that you intend to stay at for the next 5-10 years.
First thing to do is to check your Human Resources Policy. Some companies frown on coworker relationships. If you decide to break the rules (which many people do) just understand that it might not look favourable on you if you plan to stay at the company for the long-run. Promotions and potential lay-off decisions are all impacted by your reputation and how you are seen by others. If you are seen as a rule-breaker or your dating/relationship situation causes drama that is noticed in the office, it won't look good on you.
Important Note: If there is a hierarchy difference between you and this prospective love interest then it's very likely prohibited by company rules and may end up costing you your job.
If your company is open to interoffice romance, then you need to consider this: If you date and you end up breaking up, are you prepared to see your ex-girlfriend on a day to day basis and deal with all the post break-up drama in a public setting? Many breakups end in an ugly way and if you work with her, there is no escaping the free-fall. Also, is she the type of person that can be mature about things? If she is young and naive do you really want her hanging by your desk all-day, needing constant attention while you're trying to work or gossiping with others about your relationship around the water cooler?
People who work at the same office can have relationships as long as they are basically not noticeable to others. Keep your interactions with her during non-office hours. Don't use the office email to flirt with each other and don't play footsies under the boardroom table. Nobody should be aware or inclined to believe you have anything other than a totally professional relationship. If you have any doubts about either of your abilities to act this way, then I would highly caution you about proceeding.
Lastly... if all my cautions don't apply to you and it's green-lights ahead and you think you could have a real relationship with this person, then let things move forward at a slow and consistent pace. You want to be pretty certain that she is also interested in you. Don't forget that in an office environment, people are basically trapped when it comes to being nice and friendly to their coworkers. You want to make sure that she's not just chatting with you because you're coworkers. In a bar, someone who isn't interested can just tell you to f-off and avoid you, but in an office, everyone has to be nice to each other and if you're hanging at her cubicle often, of course she's going to be friendly and welcoming. It just may not be tied to any sense of romantic interest.
If you do have a strong sense that she's into you or if your flirting is being reciprocated then why not start out by going for lunch together to get to know her better. Find out her interests (maybe she loves kayaking on weekends or maybe there's a movie that she's been dying to see) and casually ask if she'd like to hang out or do those activities with you. Be very low-key about it at first. I wouldn't go for the suggestion of a big romantic splashy dinner. If she's interested in doing "friendly" activities with you outside of office hours, chances are probably good that she might be into you. Then you can take it from there. But if she puts you off or says no, then no harm done because it was just a casual suggestion and you can always explain you didn't mean it in a romantic way.
Once you are on the 'friendly' get together and not in the office, you can put stronger feelers out for whether she's into you and proceed appropriately from there.
My opinion...... never get envolved with a co-worker.
Lots of bad outcomes are possible in a relationship with a co-worker. I wouldn't get involved if I were you.
