Woe Is Me! is a series in which The Swaddle team indulges your pity party with advice you’ll probably ignore.

“There’s a woman in my office, and we’re great friends. I feel something more for her, and I believe she feels the same way, though she’s never stated it outright. I’ve wondered about asking her out on a date — she’s single, I’m single. I’m worried about how this will affect our dynamic as colleagues and as friends. How should I proceed?”

— Friends and lovers

DR: Office romances can be really tricky to navigate. In theory, I would always advise against them. However, I do understand that, often, not acting upon our feelings — especially when they’re reciprocated — can be difficult, if not impossible. Against my better judgment, I’ve done it too. But before you embark on this path, I hope you remember that no matter how badly you might want to, you can’t undo it. Also, the consequences of one’s personal and professional worlds colliding aren’t the easiest to handle — how well you fare at it might depend on the kind of person both you and your love interest are.

For the sake of your job, I’d also urge you to ensure that your organization doesn’t prohibit romantic relationships between colleagues. Also, I’d suggest you take a minute to weigh your prospects if things go south between the two of you: can it impact your career trajectory in this organization? Is there any possibility of side-picking-driven ostracization from your co-workers, in case of a fallout between you two? If one of you is senior to the other, are you sure entering into a relationship with this individual won’t lead your colleagues to accuse you or your colleague of favoritism when either of you gets promoted? On a similar note, if both of you are on the same level, do you think one person getting promoted over the other can breed jealousy? I’m not saying each of these is a dealbreaker per se, but they’re all things I think you should seriously consider.

Having said that, following your heart might also lead you to a wholesome adventure — it’s a gamble, after all. The question is: is it worth it for you?

RN: I think office romances can be quite heady in ways that not too many others are. But with the additional joy of the excitement and adventure come additional considerations: are there uncomfortable power dynamics involved? How closely do you two work together? That being said, the romantic in me says to throw all caution to the wind and go for it — as long as you continue to fulfill your contractual obligations at your job, it isn’t any organization’s place to stop you from following your heart. And besides, workplaces are where we spend the major part of our days. Feelings are bound to arise when you spend a lot of time with someone; and this can also be an added advantage for work itself, given that it may provide some motivation to actually go to your job and do your best. I don’t think romances should be considered any differently from friendships — and if the latter is acceptable, why not the former?

SK: As much as you don’t want to hear this, I’d argue against doing anything in this scenario. What if, and hear me out, you let the friendship be as is, untouched and unadulterated by the complexity of feelings? We know the script of romance all too well; the giddiness is thrilling and new and can feel life-changing. But there’s something to be said about platonic affection too; this is also love, one that promises longevity like none other. Maybe the reason she’s not saying anything is that she values your friendship more than any form of romantic relationship too. I understand it’s not a switch that can be turned off at your command, but there’s merit in trying to preserve the friendship for what it is; protecting the shared understanding and comfort you have with another person that is so terribly hard to come by. Are you willing to sacrifice what you already have with her — this unalloyed reservoir of support and love — in the hope of something more? Between workplace romances and workplace friendships, it is the subtle generosity of the latter that wins my favor.

AP: Having genuine feelings for someone doesn’t happen as often as we’d think, so please don’t let your fear or inhibitions get in your way. So many friends and colleagues date successfully. Just go for it, man. But please make sure to tell yourself that should she refuse, you’ll find a way to accept it without necessarily making things awkward with her. Telling people how you feel about them isn’t actually as complicated as we make it. Either she likes you back and is willing to go out with you, or she doesn’t and she refuses. The worst that can happen is that it will be a bit awkward for a week, but a sincere friendship won’t break over something like this. Shoot your shot.

VS: Asking someone out for a date does seem overwhelming but don’t overthink it. It could be a simple, “Would you like to grab a coffee sometime?” or “How about a movie this Friday?” If you want to be more honest and clear, you could compliment them, tell them what you like about them and that you’d love to take them out on a date. If it’s still seeming too up front, maybe try reacting to all their Instagram stories. Okay maybe not all of them. Slide into their DMs with memes, establish some comfort, and then initiate? But I’d still suggest that you go ahead and ask them out and get it over with. Then at least you will have an answer if they are even interested and in case they are not then you can move on and start pining for someone else.