A (Very) Delicate Situation

by Andie
(United States)

It's a well-known fact at our workplace that this guy is terribly shy when it comes to girls. When I admire someone, I feel the same way.

When I started working, we barely spoke. His sister (my age--he's a bit older) works with us as well, and I got to be more friendly with her. Eventually, he and I opened up to one another and began talking regularly--and have similar interests in music, entertainment, humor, etc.

This went on for about a month and half, before I finally gathered enough mental strength to put myself out there and ask him out. The deciding factor was an incident that took place on our last day working together. He'd been "crushing" on a regular for several years, and in his last days, he wanted to give her his number. After a lot of confidence-bolstering, he did it. Ten minutes later, he called the store and asked specifically to speak to me about it. We chatted, and, for my part, if felt so comfortable (he was hopeless, in a good-natured way, about the girl calling him, and just wanted to talk to someone about it).

That was the point that I realized how much more I wanted from our relationship, and knew that if I didn't act soon, he probably never would. Because of past experiences, I was very careful to conceal my growing affection for him at work (though there was a certain intensity whenever we looked at one another), and even if I had given signals, there's no guarantee he would have done anything, being shy. His sister told me he was very, very surprised when I did ask him out.

When I did, he responded with a depressing "I appreciate the gesture, but I'm going on a date this week and want to see how that pans out." Not the end of the world, but not encouraging, either.

The next day, he stopped in for coffee, and I reverted to my previous level of shyness, acting like I didn't notice him. We didn't speak, didn't even look at one another. After he left, his sister, revealed that he'd been flattered by my offer and had exhibited a degree of interest; however, according to her, he is a one girl at a time kind of guy. She also revealed that the "date" was in fact one of the blind variety, with one of her brother's best friend's girlfriend's friends (essentially, a nobody to him), and that the girl was a bit strange. Basically, she told me that there was still a high probability for turning the situation from nothing to something. She actually seemed a bit excited by the prospect.

So, I mulled everything over for a few days--went about my life normally, went out with friends, enjoyed the benefits of being single. It occurred to me today, however, that acting as I had when he visited the day after I asked him out could have destroyed any confidence in a further relationship he may have had, so I told him that I thought it was well and fine that he only take one girl out at a time, but if things didn't work out with his date, he still had an admirer. I also admitted to being painfully shy myself, which doesn't scream volumes about my confidence--though, I am a naturally confident person and had demonstrated such after we initially broke the ice a few months back.

I suppose I just wanted to assure him that I was still interested, while trying to sympathize with our shared "condition." I feel like I may have fouled up by pushing the issue though, and I don't know what to expect--or if I should expect anything. It's taken me years to come to terms with my goofy, awkward personality, and this has been the first time in awhile that I've actively pursued someone else. I just wish someone could give me a heads-up as to whether this is a lost cause, and if not, what I should do to keep it from getting to that point...