By Chadwick Matlin, contributor

I am at a loss. Not, for once, of my money. (I’ve had a great few months.) I’m at a loss of what to do about somebody I like. It’s not that she doesn’t know who I am—we’ve known each other for years and worked our way from friend to enemy to frenemy and all the way back again. She’s great—underappreciated by everyone else, but she comes with a good legacy. She’s just had a rough go of it these past few years.

Recently I started flirting with her again, not with any real purpose, but not with any real restraint either. It just feels so good to be a player. To feel like my life could change with one chance meeting in a corner office or boardroom. I’m not even sure if she wants me — like I maybe, sortof, but not really want her. But I think we have a lot in common, and we could really complement one another’s personalities. We’re both figuring out how to live in this new, crazy, mixed-up world that surrounds us. It feels like we could be great partners in existential angst.

But how will I know when I know, you know? I’ve paid people to be my friend and give me advice, but don’t I need to make this decision for myself? When will I be able to take the plunge and stop pussy-footing around?

–A.O.L., 21, New York

Dear A.O.L (AOL) :

You’re still hung up on this Yahoo! (YHOO) ? I looked through my files and I saw that you sent me more or less the same letter two years ago, when you were living still living under your parents’ roof in Dulles, Virginia. (I’m assuming this “Time Warner” (TWX) guy you mention was your legal guardian?) Now you’re on your own and you’re still flirting single-mindedly. Proof that you really care. Or that you’re a stalker.

Now, it’s possible you’ve written me this letter for the same reason you may have hired those new friends: to get your yahoo to pay attention. Not the worst idea; proclaim your interest publicly and it could be seen as a romantic gesture. It’s no Say Anything, but it’s a start.

But this has gone on long enough. I did some research and found that you’ve intensified your I-love-her-I-love-her-not routine in recent months. In October you talked to others about the best way to acquire what you desire, because you aren’t big enough to do it all by yourself. And when people ask, you’re all too happy to name-drop that you’re interested in her if it makes sense, but that you could also sidle up to others too. Nice try, playing coy.

But I’ve read up on your yahoo, too. And it doesn’t seem like she’s eager to get together. In fact, she bought a can of mace from Goldman Sachs in case you try and make any unwanted advances or hostile takeovers.

Yet, my advice is this: Don’t be deterred. To answer your original question: How will you know when you know? That you think you may already know means you know. That’s how love works. The confusion is the proof. QED.

The time is right to make a move. Your house is in order. As you said, you’re making money again, and even have enough lying around to buy yourself some expensive, delicate baubles. You need what Yahoo can offer you now: more attention, more purse strings, and more energy to compete for supremacy.

Now, you may not have the perfect relationship from the start. The power differential will be steep, and both of you may have to get rid of a few people things to make it work. Your yahoo is going to be the breadwinner and then some. Which is why she may not sign on for a traditional partnership; if she won’t go into this willingly, maybe you can pitch a political marriage, one of convenience for both parties. Partner first, procession down the aisle, later.

So stop flirting and start committing. Even though you’re 21, now’s no time to be a bachelor out there.

10-k (ten thousand, that is) kisses,

Mergie

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