For Smiley, Who Wants a Certain Guy's Attention

It's Saturday morning and time to plan some serious fun. In the meantime, the writer of the following letter originally posted it in the comments area, where I answered it. I'm afraid she'll miss my response, so I'm reposting it here with a couple of additions:

Hi Terry,

You remind us time and again we are precious beings who deserve nothing but the best.

Hoping to seek your advice on something. There's this guy that I like. We've been going out in a big group with other friends for the past few months. We laugh, talk and have a lot of fun when we are out.

However, I am always the one to organise the big-group outings, and he has never asked me out on a single date. I suppose that means he's not interested in me in the romantic sense. Well, so how can I attract his attention, let him see me in a different light, and make the necessary moves?

-Smiley

Thanks for writing, Smiley. From the tone of your letter, it's easy to see that you are a special being who deserves nothing but the best.

You say that you have a lot of fun with this guy when you're in a big group. Now, do you make a special (but casual) effort to speak to him on his own? Are you smiling at him and making eye contact?

If so, and he's not picking up on it, you could be so bold as to say, "Hey, I have an extra ticket to ______________. Would you like to go with me?" (Since you're the one who's usually doing all the organizing, this wouldn't look at all outlandish.)

If he says yes, congratulations and good luck. You'll get that chance for him to see you in a special light. If he says no, it's his loss. Take another friend and have a great time!

Whatever happens, keep doing what you're doing. By taking the initiative in getting people together for fun, you exponentially increase your odds of meeting your perfect guy.

You're no down-on-your-luck complainer, that's for sure! You make things happen, and that's highly attractive.

I salute you.

-Terry