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There is a person I've met at the workplace who I've become interested in since I was introduced to on my first day at work. The development of our relationship was slow due to being in a different department but we eventually got close enough to say that we're friends (she said to me that we're already friends) and go out for lunch with other colleagues as well every now and then.

After knowing each other for half a year, she got herself a boyfriend and to save money, she tends to buy a lunch box and eat in the office instead of going out. (Japanese setting)

About a month+ ago, I sort of heard something that she doesn't have a boyfriend now and I have always been thinking about confessing my feelings even when she had a boyfriend but couldn't because I am somewhat of an introvert or a person who doesn't speak much or just a coward who is not courageous enough.

We are both in our 20s (she is 2 years younger than me) and I wonder if it'll be awkward to ask her to meet for a couple of minutes after work to hand her a love confession letter personally.

It has been 3 months since I got moved to another office back in June 2017 so I think I can only ask her to meet me at some train station in the middle of her route going home from work.

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    Hi josephting, a few of the answers so far are focussing on whether or not the letter is the way to go. I’m just wondering, is it pretty normal to give/receive confession letters for your age group, in a workplace setting? Or are you considering this route because you are shy? I think whether or not this is a commonplace thing would greatly change the answers: for example, if this is what is ordinary in Japanese society, a Japanese woman could actually feel more comfortable receiving a written confession than a verbal one. – sudowoodo Aug 31 '17 at 16:08
  • @sudowoodo Yes, that was the question I want answered. To be honest, I don't know how it is around here. People don't go and tell people that they have confessed to other people let alone how they confessed to the others. Yes, I was worried that I couldn't get my feeling across just by speech. I'm not planning to do it in front of other people anyway so it's probably going to be if she is comfortable with me or not. – josephting Sep 1 '17 at 4:21
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Being an introvert is not a problem. I am an introvert. That means that talking with people makes me tired instead of the opposite. While it's true that I became uninterested in other people and quite shy as a consequence, I have currently no issue talking with strangers, even about embarassing stuff.

That's because being an introvert only means that social interactions are exhausting, it doesn't make you terrible at these interactions, having poor social skills do. You can develop these skills if you put some effort on it, and if you don't it will always be that hard to interact with people and introvertion won't be a valid excuse.

Regarding the issue your question is about, you should first question you intents. Is it about the both of you or only about you?

I have always been thinking about confessing my feelings even when she had a boyfriend

You state that you consider her as a friend and that you love her, but at the same time that you had a constant desire to confess to her regardless of her romantic availability.

You need to ask yourself the good questions:

  • How do you think she would react to you confessing to her?
  • How would she react to the particular way of confessing you mentioned?
  • What do you think you would bring to her that would make your presence as a lover valuable? Why would you be a better match for her than other people?
  • Among these things, which do you think she already perceives in you and recognize as such?
  • What difference does it make to you whether she has currently a boyfriend or not?
  • What would be your reaction if after confessing to her while she is already with someone else, she turns you down?
  • What would be your reaction if she told you she rejected you because she is already with someone else?
  • What would be your reaction if she told you she rejected you only because she is already with someone else, and that otherwise she would have accepted?

I believe that if you do it seriously, you may find your own answer.

But for Pete's sake, please, try to not do the letter thing, it's the worst thing. You are basically handing it to a person, who will then read it, taking notice of whatever content you put in it, maybe becoming very embarassed in the process, and then it wil be her responsibility to reach you about it. That's even more embarassing.

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    To be honest, I've hidden my feeling for long enough to the point that I don't want to care anymore but to confess my feelings. I let myself taken over by emotions there. My social skill is not good I suppose especially around many people. It'll probably be OK if it's just the two of us. Guess I'll ask her out more seriously and take it from there. Thanks! – josephting Sep 1 '17 at 4:16
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    "I've hidden my feeling for long enough to the point that I don't want to care anymore but to confess my feelings" You still have to respect her and her feelings, or it's just about you. – ksjohn Sep 1 '17 at 7:07
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    Of course. What I meant was I don't care what's going to happen to myself anymore and just want to go for it and see what she thinks. Keeping that feeling in any longer will not change anything but will only be a measure to protect myself. – josephting Sep 2 '17 at 8:29
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    @josephting you really honestly would be okay with her not giving any answer back? Do you really think either of you can be friends after that kind of declaration? I think you're kidding yourself. – Kat Sep 5 '17 at 20:27
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    @ksjohn It struck me hard when you say to act like an adult cause I think I'm acting like a kid. Still, I might be taking references from love movies subconsciously albeit not just from Hollywood. Now, I'm thinking about inviting her to a boat cruising party with other friends and acquaintance and take it from there. Wouldn't even know if she'll go which led me to wanting to just let her know of my feelings. All the input here have given me good insights. Thank you everyone. – josephting Sep 7 '17 at 1:19
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Being an introvert, you prefer to write how you feel.

However, a love letter could make things awkward early in a friendship. You are just friends who haven't been alone with each other yet. You don't know how she feels about you, do you?

  • She may only see you as a friend.
  • She may like you but is shy.
  • She may be seeing someone else
  • She may not want to be in a relationship right now

You won't know until you get to know her better. If you are already friends (does that mean you have her phone number?), do you feel comfortable asking her out on a date?

If she says yes, that might mean she likes you and wants to get to know you better but if she says no, as disappointing as it might be, it should still be less awkward.

It is very sweet of you to want to hand her a love letter but imagine how much more romantic it will be if you wait for when the time is right and when you have already gone out on a few dates and she has shown that she likes you a lot, too!

  • Our relationship is kind of awkward to begin with. We don't often talk with each other when around other colleagues but sometimes chat with each other both at work and on LINE. I have asked her out on a date a couple of times but they were done on a whim. She naturally already had plans as it was of a short notice. Guess I'll ask her out more seriously and then go from there. Thanks! – josephting Sep 1 '17 at 4:12
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If you have her phone number I would ask her if you can meet to drink something or just talk. If you don't have her phone number try to talk with her when you see her at the train station. Don't confess your feelings at the first meeting. I don't think that this would be a very good idea. Could be a bit awkward for her and maybe even for you.

You said that you are more of an introvert person. If you have a problem to confess her your feelings it is easier for you to write a letter. To be honest I think it's better to say that from face to face so you see how she reacts to it.

So try to ask her if you can meet her after work to just talk a bit or just hang out. Wait a bit until you try to confess her your feelings. After some time your relationship with her gets better and better and then it's way easier for you to tell her everything. If that is always too complicated and too hard for you then try to write a nice letter.

  • Thanks for your answer. Well, now I might as well do both then. :D We have met each other quite a bit albeit with others as well, not just the two of us. – josephting Aug 31 '17 at 7:15
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First. Don't confess yet to her. You stated yourself that you sometimes hangout and that you are friends. You like her, and with a little luck, she likes you. But that is all. It's not loving.

Second. Give yourself a chance to really know her and get in love with her, same goes for her. Try going out with her alone to the movies, dinner, just shopping, maybe a concert, be there for her when she has problems. Talk to her about the things you like, get her to open to you. Have fun together. After all that. Then confess to her. A lover is your best friend, someone you can depend on.

Third. I'm an introvert person too, but experience has taught me that it is not ok to express your feelings in a way to shield yourself from a rejection, like a letter. That is disrespectful to the girl you like. Take into account that relationships are also about exposing yourself to being hurt, she probably has done it before in her past relationships, and if she accepts to be in a relationship with you, she is taking that chance too. Don't be afraid to be hurt, you will learn how to deal with that and it will help you in the long-term.

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