Boy meets Girl, Girl already has Boyfriend...

So what is Boy to do?

Pursue, pursue, pursue.

So here's the scenario. You're a nice guy, a Gentleman, and you meet a really nice girl, a Lady in every regard. She's bright, funny, charming, and attractive in every way.

You'd be perfect together. Your conversation flows effortlessly. There's the right combination of ease and tension that you feel you could discuss the deepest of topics (and probably have) all the while her playful jabs keep you on your toes. She shares just enough similar interests that you never run out of things to talk about, but you're different enough that you both keep introducing new things into each other's worlds. There's even a slight spark, a physical chemistry you try not to notice when you give a friendly hug goodbye. She's your friend after all - and she's taken.

You're a nice guy, so your instinct is to hold back, silently disguising your true interest. Maybe you even convince yourself for whatever reason that she's not really the girl for you. It's not your style to step on another man's toes either. You'd never think to create problems or cause drama.

Here's the deal though. This other guy, he's probably a douche-bag. And even if he isn't a douche-bag he's probably not everything she's looking for.

Woman (and men) tend to maintain relationships well beyond their expiration date. They get comfortable. They don't want to be alone. They convince themselves that they can deal with the negative aspects of a relationship because they'd rather not bother with the uncertainty of moving on. Sometimes they even stop believing that there's someone more compatible out there - and even if there was they'd probably not be interested.

In short, they get stuck with Mr. Not-Quite-Right because Mr. Right doesn't ever seem to come along.

Well guess what. Mr. Right hasn't come by because Mr. Right is a Gentleman. And like you, he doesn't go around hitting on another man's woman.

We need to fix this. Chances are she's not going to leave Mr. Not-Quite-Right until someone else shows up and shows interest. Help her out. Don't let that next guy be another Mr. Not-Quite-Right instead of you.

So what do you do? Be direct. Lay your cards on the table. Let her know she's on your mind. Be a complete Gentleman and don't cross any relational lines that could get you in trouble. Instead drop a comment or two and then gracefully return to normal conversation.

Tell her, confidently and comfortably, that she's quite the catch (a compliment everyone likes) and that if she were single you'd have no hesitation asking her on a date, but of course you couldn't do that while she's with someone else because you're not that kind of guy. The end.

Don't drag it on, don't push, and don't even bring it up again either. Just plant the seed and see if the tree grows.

If she's really your friend and you're a genuinely nice guy she'll take it as a compliment and that's that. If somewhere inside she harbors a certain interest and a dissatisfaction with the guy she's with, she'll think of you. She'll know you're an option should things change.

You can't force anything to happen, and that's not your style anyway. But at least this way she knows a knight in shining armor is waiting, but let her determine if she needs rescue or not first.