He's Nervous about Asking Coworker on First Date

Dear Papabear,

Thank you for reading this letter. The last time I sent you a letter you helped me a lot in picking my fursona according to my personality, and I must say that I feel accomplished now.

However, the dilemma I now face has nothing to deal with fursonas or the Furry Fandom itself (at least not directly). My newest problem is related to love.

Allow me to explain.

I obtained my degree in Translation a few months ago and am now working at an airport as a flight dispatcher trainee. 

Two weeks ago, a new female employee started working at the department opposite mine (I work in the air operations control centre, and she works in the ground operations control centre). 

We see each other almost daily, and I could not help but notice that she looks at me and smiles at me a lot. And I do the same. I appreciate her presence, for the look on her beautiful face is that of an angel. 

Over the days I have become ever more infatuated with her. Every time I see her I wish I could tell her what I feel for her. She is beautiful, intelligent and kind, and I'd love to be by her side as more than just a colleague or a friend.

However, I do not even know how I will let her know that I like her. I have never dated anyone before, and I do not wish to scare her off. Furthermore, Seeing as we work in different departments, it would seem strange to my colleagues if I were to simply walk in and talk to her, especially because we both have too much work to take care of. Planes do not fly by themselves.

I thought about waiting for her as she comes to work or as she leaves work, but we are on different schedules, and it is therefore impossible for me to do so.

I do not plan to tell her about the Furry Fandom or anything alike, considering the possibility that it may reduce my hypothesis to have a relationship with her. But will doing so suffice?

I do not know what to do. I do not want to destroy the friendship we have, but what if she is "the one"?

Should I talk to her? If so, how?

Best Wishes,

Armand DeCrow (age 21, Lisbon, Portugal)

* * *

Dear Armand,

I’m glad I was helpful with picking your fursona and hope I can help you a second time.

My understanding of Portuguese culture (and correct me if I am mistaken) is that it is a rather formal one. I am also unfamiliar with workplace etiquette in your country. In the United States, some companies have rules about personal relationships at the workplace. I imagine that the same might be true in Lisbon. It might be a good idea to check company policies in this case, and, of course, it is important that your personal life not interfere with your employment.

Given this, I agree with your idea that you should try to talk with this woman outside the workplace, even if it is just outside the building. Address her formally as “Senhora” (did I get that right?). I think it would be a good idea, to start, and to make things possibly less intimidating, to ask her to some kind of group event, such as a party with your friends. Something that is not one-on-one. At this function, whatever it might be, that’s when you get to know her, see if you have things in common. And, if it goes well, then you take it to the next level, which is going on a real date, one-on-one, to a restaurant or the cinema, or something like that.

To answer your question more directly—YES! You should talk to her. If you approach it the way I describe above, you should be fine even if the date doesn’t go that well. You say you are worried about destroying a friendship, but this isn’t a friendship yet. It is just smiles across a hallway, or whatever. You have to have a friendship first before you can worry about messing it up, silly man.

And don't worry about the furry stuff. You can decide about that later after you know her better.

You’re 21, and you are looooooooooooooooooooooooong overdue to start dating. So, don’t be afraid, and don’t make excuses. You like this girl, so go for it! You have nothing to lose. Go ask her out, and when you do, just be direct, and be yourself. Don’t overthink it. Tell her, straight out, that you like her and you’d like to get to know her better, and invite her to that first outing.

Good luck!!

Papabear