No one wants to think about the end of a relationship at the beginning of one, but when it comes to workplace romances you do need to think about that. What happens if this does not end well? Would you be willing to quit your job if it became too uncomfortable to see him and work with him every day?

Workplace issues aside, you ask an excellent question, “is this a great idea?” For that you need to look at your current situation. You said that this is someone you’ve known for a long time, that’s a great start. It doesn’t sound like you’re rushing into things. You mentioned that you’re friends and that ” it is obvious that there are feelings involved in our friendship”. My question to you is this: is it as obvious to him as it is to you? Generally speaking, if a guy wants to ask you out, he’ll ask you out. I have never yet met a guy who didn’t ask someone out because he “didn’t want to risk the friendship”. That seems to be something that exists in women’s brains but not in men’s.

Is there some other reason why he would not have pursued a romantic relationship with you up to this point? Were you unavailable? Was he unavailable? Was there a misunderstanding? Have your needs or his needs changed? If there was something that was in the way before that is no longer in the way then yes it might be a great idea to tell him that now that things are different, you’re interested. However, if nothing has changed, if you’ve both been available and he has made no move toward you then it may simply be because he sees you as a friend and not as a potential girlfriend.

I would suggest starting with something a little less risky than a love letter. Ask him out for coffee instead. Friends go out for coffee, so do co workers. Spend some time with him and see how the conversation goes. You should be able to get a better feel for what he’s thinking. If you think he’s interested, ask him to dinner.

Love is always a risk, but declaring your love right off the bat is a huge risk with a lot of potential for embarrassment, especially since this is someone you see every day. Start small but deliberate and see where the day takes you. Love letters almost always work best in the context of a committed relationship.

One of the reasons that people don’t often marry the person that they think they are in love with at 16 is because they still have so much growing up to do and will change a lot before adulthood. With each life experience we encounter we change and our perspective changes as well.