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A coworker and close friend of mine is in a serious relationship; one day she may well marry her current boyfriend. Even so, I’ve had strong romantic feelings for her for approximately a year. I’ve done my best to keep it under wraps, both to respect her current relationship and to keep her from feeling uncomfortable around me. We never work with one another, but (when there isn’t a global pandemic!) we eat lunch together nearly every day and run in the same circle of work friends; telling her how I feel would probably disturb that current friendly arrangement at least for some time.

With all that said, bottling up my feelings has been extremely trying. On the outside I’ve done well enough so far at treating her as just a friend, but internally I’ve been turbulent, tumultuous, and unstable. I feel something like a kettle about to boil over. I believe sharing my feelings with her, with the understanding that they’re not reciprocated and that I expect nothing from her, would spare me a lot of future pain and help me to regain balance in my emotional life. At the very least, I would no longer need to harbor the secret, and could eliminate the irrational sliver of hope which says I still have a chance with her.

So, in the interest of restoring my peace of mind and helping myself move on, I wish to put my cards on the table and disclose my feelings to her. If this is permissible, what must I keep in mind as I broach the subject? Can I tell her in a way that will be mature, respectful of her and her relationship, and won’t make her feel uncomfortable sharing a workplace with me?

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    Is there any reason why you want to share this with her other than your own emotional distress? I am asking because telling her will possibly put stress on her both in workspace and friend circles, and if it is only for you own relief, it might not be ideal. However, if you have alternate goals, such as exploring mutual feelings, then that changes the scenario. – Jeroen May 20 '20 at 8:53
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I'm not sure this is possible. Knowing someone has romantic feelings for you changes the dynamic, and things are almost certainly going to be awkward for at least a while. If you truly don't expect anything from her and want your relationship to stay the same, you're probably best off keeping your mouth shut. However, if you want her to squash that tiny iota of hope you're harboring and relieve yourself of a secret, it may be possible to do that.

There's no guarantee your confession won't ruin things, but there are a few things you can do to minimize the risk. Personally, if a friend told me they had a crush on me but weren't expecting me to do anything about the knowledge, they simply wanted to tell me, I wouldn't believe them. People confess romantic feelings because they want a romantic relationship. If you don't want anything to change, then why bring it up? Ask yourself if you're truly okay with her turning you down completely and unequivocally. Be honest. If you can't, then this is probably a terrible idea. She's already going to doubt you'll be fine with it, and that's what makes it awkward. To get around this, you'll have to provide a convincing and sincere reason for telling her other than seeking a relationship.

Luckily, you've got a fairly convincing reason in your question: you know it's absurd, but there's a tiny voice telling you that if you never say anything, you'll never know for sure she's not interested. You want to say something so she can tell you straight out that she's completely uninterested and you have zero chance. Say that. If she tries to soften the blow when she says no or seems uncertain how to respond, reiterate that you truly need a devastating rejection so you can put the idea to rest for good and move on. She's going to be hesitant about turning you down because she won't want to hurt you, so let her know you won't be hurt and you fully expect rejection. Be upbeat and sincere, and maybe she will believe it and be honest.

Although I've not been in this exact situation, I do often ask people if they want to do things that I want them to feel zero pressure to agree to. I've had good results with cheerfully telling them "you can say no, I promise, it's totally fine." It often gets people to admit they aren't really interested. Especially if there's a reason I expect they'll probably say no (short notice, likely to already have plans, etc), then I'll even preface the request with something like "I know you'll probably be unable to, but I figured it doesn't hurt to ask just in case you happen to be interested and available..." It only works when it's sincere though, which is why I say not to try this unless you really mean it.

After she confirms that no, she is not interested, thank her with a positive attitude. At this point I'd probably acknowledge she's probably feeling awkward and uncertain about how things will be between the two of you. Personally I'd make a joke like "so... How long should we be awkward around each other?" Don't pretend like your confession should have no effect on her whatsoever, that's not fair.

Hopefully she'll laugh it off and say things will be fine, but it's possible she'll want some space. That's her right, and it's the risk you're taking by telling her you have romantic feelings for her. Even if she wants to stay friends, she may feel like she's betraying her boyfriend by being close friends with someone who likes her. It's possible he's a jealous person and has already expressed concerns about you. Maybe a part of her is attracted to you, and that will make her decide it's too risky to her relationship to be close to you. There are lots of reasons outside of your control that could cause this to end badly for you even if you do everything right.

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You say that you want to tell her because you think it will help you move on. There are two major errors in this thought:

  1. Moving on is a gift you give yourself, it is not something that someone else has to (or, often, even can) do for you. If you truly want to move on, you need to get out there, meet more people (both men and women), maybe find a new hobby, and build up a good life for yourself without her. Maybe you'll get interested in another woman instead, maybe you won't, but the point is to enjoy your life enough on your own that you no longer feel a need to make her a part of it.

  2. Even if you do tell her, it won't help. When I was a teenager, my first love was a girl who was dating one of my friends. She and I were also very close friends, and I told her how I felt about her. She (and everyone else) knew I was totally crazy about her, but we were still able to maintain our friendship. None of this made it any easier for me to deal with or get over my feelings for her - if anything, it made it even more painful to be in that situation, and made it harder for me to move on.

Also, in my experience, women tend to be pretty good at picking up on this sort of thing, so there's a good chance she already knows (or at least suspects) how you feel. The kindest thing you can do - for both of you - is to allow her to remain unaware of your feelings (or at least to continue pretending to be unaware) and move on romantically without trying to force the issue with her.

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Imagine your reaction if your feelings aren't mutual

When I was in high school I had my first partner. A few months after that my best friend started acting a bit strange towards me, they seemed to always be down around me and wouldn't talk to me as much as before. After me asking repeatedly why they were feeling down and telling them they could confide in me, they told me they loved me and that they kept the secret because I was in a relationship and so it seemed that their love couldn't be reciprocated because I was with someone else. I indeed didn't love them back and we remained friends, but they were very distant for a few months after that: they told me afterwards that they had to take some time to accept the situation so we could go back to being friends. Which is why I invite you to think about it - if she tells you she doesn't feel the same way about you, even if the confession doesn't make her feel awkward, how do you think you will feel? Will you be able to go back to how things were before?

Confessing feelings can make people uncomfortable

Today's society isn't very inviting to demonstrations of affection. We're not used to tell people we like them or that we think they're great - we'd rather show than tell. So when someone tells a person they love them - which is supposed to be the biggest form of affection towards someone - it can make things very awkward for the latter if they don't share these feelings. So even if you don't think you'd be uncomfortable with her not reciprocating your feelings, maybe she will be uncomfortable for not liking you the same way you do. It might put a strain (even a temporary one) on your relationship. I believe that things could go back to normal after some time, because that's what happened to my best friend and I, but I think this happen when you've had a strong bond before and that you both care enough about the relationship to preserve it after this happened.

Be honest about why you think you had to tell her

Given the risks I mentioned above, I wouldn't confess to her. You have a great relationship, but work is involved and that makes things more complicated. You don't know if you might have to work with her in the future. Your coworkers may be made aware of your feelings and even if she trusts you and cares for you, maybe some of your colleagues could see it in a different light and use it against you (the worst thing I could think of is them accusing you of harassment at the workplace). But I understand you want to be honest with her so what I'd advise you to do is to make it clear why you're telling her:

Hey Anna, there's something I need to tell you. There's no easy way to say this but I think I have feelings for you. I'm not expecting you to feel the same way, and I'm telling you because I value honesty and thought it might help me moving forward. I really hope this won't change our relationship because I care about you as a friend.

With such a phrasing you tell her why you had to confess and what you're expecting from the confession. It also lets her space to tell you how she feels about you. This does not guarantee things not to be awkward between you (even for some time) afterwards but I think it's the best way to convey your feelings without embarrassing her if they're not mutual.

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