I had no memory of this scene whatsoever, so I went back and rewatched it real quick on youtube. And the thing I love about it …
Okay. So Wesley is extremely uncomfortable here, and it’s for extremely teenage boy reasons. He doesn’t think this is his style, because it’s too much. Too romantic, too sincere, too over the top. He’s afraid he’d be laughed at, he’s never going to say words like that to a real woman.
But Will Riker, full of confidence, argues that you need to take the plunge immediately. You need to go all in, play in unsafe, take your chances. Because Will Riker’s self-confidence is godly.
BUT. But. The gifs don’t quite show this, but if you watch the scene. Right after his opening, ‘you are the most beautiful woman in the galaxy’, and just before he says ‘but that might not work’, there’s a tiny moment where Wes and Guinan share a look, and that look is amused. Slightly incredulous. And that’s where Riker immediately dials back and goes ‘but that might not work’. He only comes back and goes all in when Guinan goes, no, no it would, and basically gives him her blessing to follow this path. Which is where Will, having permission, knowing this is what his conversation partner wants and enjoys, goes in and gives it his all.
And Wesley’s expression, incidentally, slips and becomes both embarrassed and somewhat concerned.
It isn’t verbalised, but that was also a great lesson on why Riker is as successful as he is. Because he asks. Not verbally, but he takes his chance, and then adjusts his approach from feedback. If she acts embarrassed or upset or amused or incredulous, he takes a step back and goes, right, that’s not the approach you want from me. But if she responds, if she indicates that hey, this conversation is in fact something she might enjoy right now, he grins and locks in and puts some effort into it.
It’s also a tiny detail, but the conversation starts, after Riker has asked Guinan over to help him, with him pulling out her chair. Even if it’s a lesson and they all know it’s a lesson, he still takes the time to get the small details right. This is a date, even if it’s a fake one. You damn well pull out your lady’s chair for her.
And in the conversation itself, he and Guinan are having genuine fun. They’re playing off each other. And they address the ‘sincerity’ of the play-acting. Because flirting, ‘lines’, always have an air of artificiality to them, but their fake flirting actually addresses that. The line is a ‘knock on the door’. It’s fake, but it’s an indication that the other person is willing to put some effort in. To say things to make you feel good, and have a good time in the conversation. There might or might not be anything serious happening behind them, but the game can be fun in and of itself, and you never know, something might develop from it. Guinan is having genuine fun. To the point that she doesn’t need it poo-pooed by a teenage boy, and tells him to shush while she enjoys a man having taken time out of his day to flirt outrageously with her.
Wesley doesn’t get any of this. He doesn’t understand more than the words that are happening. But there are actually a lot of good lessons in here. To take it less seriously, to be willing to be foolish and embarrassed, because it’s not life or death or the end of the world, no matter how much if might feel like that to a teenager in love. To take it more seriously, to be willing to say things that are rich and expansive and romantic, because you want your partner to feel valued. To respond to cues, to start from an overt opening where your interest is clear, so that you can see if your partner wants that or not. To be willing to go all in, if it turns out your partner does, at least right now. To make some effort, to get the little details right, to go out of your way and do the small things, the romantic things, to make the other person feel special.
Like. He probably should have verbalised more of that for Wesley, because if teenagers could pick up non-verbal cues like this they wouldn’t need lessons to start with. But it actually is a pretty good showcase of why Riker-the-flirt had as much success as he did. Because he’s responsive, because he’s expansive, because he puts the effort it, because he’s willing to look foolish, because he wants to make his partners feel good about what’s happening. He’s confident, but he’s not predatory. He wants everyone involved to have a good time. And it shows.
(And he also is a little uncertain, as well. He has self-confidence to match Q, but he is also taking chances, and when they appeared to laugh at him a little bit, he did pull back and recalibrate. His grin had something nervous around the edges. He’s afraid to be laughed at too. He doesn’t like rejection any more the next man. He’s just willing to take his chances regardless, and to take the hit if turns out he has to).
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