We’re so shy

I posted this note in the comments section yesterday after it seemed that people were not being respectful in the comments section:

Hi all,

I'd ask that people refrain from attacking one another – it's just not the point of things here. I want Love Letters to be fun, helpful -- and banter is certainly a part of that, but heckling, bullying, revealing people's personal identities, and over-the-top mean-spirited comments are not.
99.9 percent of you know what crosses the line. Those who don't will be blocked. And please, try to ignore those who do cross the line. Not worth the energy.

Now go back to being fabulous, please.

-- Meredith

Please be respectful. Please do not alienate other users. Use common sense. Those who go out of their way to make users uncomfortable will be contacted, etc.

I'm cute when I'm mean, right?

And now I ask that you help this letter writer. And read the winners of the "Love and Redemption" contest.

Dear Meredith,

Somewhat recently, I was at a party and was introduced to a really wonderful guy. We have some mutual friends, but our paths had only crossed very briefly before. Both of us are on the shy side, so other party guests were surprised at how immediately comfortable we were chatting with one another.

He was very kind and intelligent and funny and easy to talk to. He asked for my number and if he could take me out on a date sometime. I was enthusiastic at the prospect of all of this going as planned.

After the party, I learned that this was a huge deal for him to put himself out there like this, and everyone was surprised. But an important side note -- he had also had liquid courage on his side so. While he deserves credit, so does Bud Light.

All of this sounds very promising right? Or it did to me at least, haha. The next day I sent him a text just to say it was great meeting him blah, blah, blah. And he responded that he'd call me over the weekend to hang out. I unexpectedly was out of town for the weekend and let him know, and he responded by saying have a good weekend then.

Fast forward approximately three weeks and we are at another party hosted by the same mutual friend. I came to the party solo, but all of his closest friends (all of whom had witnessed our previous encounter) were there. We greeted each other but both of us quickly went back to being our shy selves.

At the beginning of the night, we didn't chat much, though our attention was clearly partly focused on one another. I would glance over at him, only to catch him glancing at me. It was as though both of us were waiting around for the other to strike up conversation.

Eventually, I decided I had nothing to lose and thought it would be worthwhile to find out why he batted zero on the follow through. I approached him and said I wasn't trying to be rude, but wanted him to know that I was disappointed he never followed through. He responded by suggesting it wasn't him that decided the outcome, or lack thereof, and acted somewhat defensive (but in a very adorable way).

Then we were interrupted, as it was a rather large and loud party. I moved on to a conversation with a friend from way back who's known for being a flirtatious charmer type. The guy I actually like happened to witness this, and knowing the charmer's ways, promptly decided to give up on me. We didn't really talk for the rest of the night and that was that. But, again, I had zero interest in the other guy. I merely gave him the time of day because I didn't want to be rude. Nor did I anticipate anyone thinking anything of it.

So now I am stuck. I can't seem to let go of this shy but wonderful guy. Ordinarily, I would just move right along but I keep thinking about how this all should have worked out, which tells me I need to find out definitively where he stands.

I keep on thinking I will run into him, but that has yet to happen. If I did, I'd be comfortable suggesting we start from scratch and try to go on a date. But I'm afraid I won't run into him, so I am contemplating sending a text or initiating some other form of contact.

However, I worry that too many mixed messages are floating around. And there are lots of questions. Would he actually want to go on a date with me? Did he really ignore because he thought the charmer would win? Wouldn't he have tried harder if he was really interested? And most important of all, has too much time passed? (It's been about a month since the last encounter).
Any advice at all would be so greatly appreciated.

– A cowardly (and somewhat confused) lion

ACASCL, you have to ask him out. He asked you once and you were busy. For whatever reason, he decided that the ball was in your court.

You're both shy. You're both staring at each other from across the room. You both want to interact but don't know how. And now he's probably sitting around thinking, "I lost out to a suave idiot who trumped me at the party. Has too much time passed?"

Call him (and I mean call, don't text). I'm not saying that he shouldn't have followed up, but I am saying that he made some big first steps. Help him out and see where it goes. A month isn't a long time, but please, do this soon.

As you put it, you've got nothing to lose.

Readers? Should he have followed up with her? Can cowardly lions date each other? Should she text or call? Has too much time passed? Discuss.

– Meredith