Breaking Down A Night As A Wingman

How A Great Wingman Will Break it Down:

A few weeks ago, I was out with my friend Alex. He is a single, well put together, and is a practiced conversationalist. Since I’m in a relationship, I’ll be his wingman for the night.

I thought it might be helpful to lay out some of the moments from the night, regarding wingmanship — here goes:

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Alex and I drive down to a local hipster cocktail lounge for a mutual friend’s birthday party. We arrive early. In fact, we’re among the first groups in the bar.

Why does this matter?

There are a lot of reasons to show up early to a party or bar. Arriving early allows us to scope the venue out, find a place to sit, and grab a drink. As the bar fills, the music gets louder, and the energy level rises – so will ours. If we had arrived late, we’d be jumping into a high-energy situation; we’d have to calibrate our energy with the crowd and the music, in addition to competing with conversations that have been going on for a while.

—-

We walk in to scope the place out and grab a cocktail. Each of us orders a particular cocktail made with specific liquors.

Why does this matter?

Choosing a specific drink shows character. There is no story behind generic. We both know what we like and why we like it and can articulate it if someone asks. This comes into play in our first conversation.

—-

Once we have our drinks, we approach the first group we see: two mid-20’s punkish hipster women. I say to them, “You two are here for John’s birthday party, right?”

They’re not, but it doesn’t matter.

Why?

Remember, the game is played with everyone in the room, not just the people you’re talking to and we are waiting for a party to arrive. When they get here, we want people to see us being social. Whether or not this first group knows the people we’re meeting doesn’t matter, all that matters is that they aren’t made to feel uncomfortable by our approach. The more engaging and energetic the conversation appears the more value it will add when our party arrives.

—-

Despite the fact that these two women aren’t there for the same party, the conversation starts. They ask us about our drinks, which leads Alex into a story about a monthly dinner party I host, and then I carry the conversation forward about traveling the world and visiting unique speakeasies.

Why does this matter?

So far this conversation is all a series of bridges and identity stories. Bridges are questions and observations that propel and steer the conversation. Identity stories are emotionally charged anecdotes about our lives that build our identity. The goal is to add value to a conversation while building up ourselves as characters in their minds.

—-

Our party arrives. Things are going well with these two women, but we say, “pleasure, meeting you” and walk over to our friends.

Why does this matter?

If you leave on a high note, you can always re-approach. In the best-case scenario, they re-approach you. Remember, it’s also early in the evening, they likely aren’t going anywhere. If Alex wants to get to know either of them, he’s got time.

—-

John, the guy who’s birthday it is, introduces us to some friends who we speak with for a few minutes. One of his female friend’s jumps in as he leaves to greet other guests. She asks, “How do you know John?”

Alex and I tell a short story about how we all met – it’s funny, she laughs – and it leads into a story about John’s passion for cinematography. During the conversation, she asks, “are they with the party as well?” pointing to the two women from a moment earlier.

Why does this matter?

This might not seem important, but it is because it shows us that the social proof move worked. She noticed us talking to the two women when we arrived, otherwise she wouldn’t likely be commenting on it.

I should note that this doesn’t mean that she’s necessarily attracted to either of us or that there’s some kind of jealousy plotline going on. It could, but we don’t have enough evidence to make that assumption. Right now, It simply means that she noticed us being social.

—-

Alex continues the conversation, and I spot a table behind him. I say, “Let’s grab that table.” They agree, sit down, and I ask, “Do you guys want a drink?”

Why does this matter?

1. As the wingman, I’m trying to improve his situation and sitting is better than standing in most situations.
2. As the wingman, I don’t sit. Instead, I find a reason to leave them alone for at least a few minutes. In this case, I’m grabbing the drinks. Even if they don’t want another, I still leave to fill my own and give them alone time.
3. When it comes to ordering drinks, it’s generally more strategically sound to get the round, rather than just to buy her a drink or just to buy a friend a drink and not her. The first can come off as hitting on, the second as cheap.

By the way, being cheap is one of the least attractive qualities you can have. Don’t pay for someone’s time, but also — don’t be cheap.

—-

He replies, “Sure, take my card, you bought the last round?”

Why does this matter?

To be clear: I didn’t get the last round, but handing me the card is a f*cking genius move. In effect, he’s going out of his way to express that he’s a trustworthy friend, not cheap, and that he’s down to improve the overall energy of the group by adding some drinks to it.

—-

I come back with drinks, they look like they’re getting along well, sitting close and deep in conversation. He seeds a bar that he loves – obviously, he’s interested in her.

The seed needs a little work, so I support it by jumping in with a story about the bar he’s suggesting. Neither of us invite her to come with us there – we simply talk the place up and recommend she visit it one day.

Why does this matter?

Because of what happens next.

—-

She says to him, “You’ll have to take me with you next time you go.” He ignores it and asks her a question about a previous topic. I see that he’s got this handled. So, I leave and talk to friends who’ve arrived.

Why does this matter?

One of the most important skills a wingman must possess is to know when to leave. He had it handled, so it was time for me to mingle with friends.

—-

An hour later, he has a date set up with her, we talk for a few more minutes, and then take off. She texts him as we drive home. She’s excited to meet up with him at the bar we seeded earlier in the conversation.

Overall, a great night.

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If you’d like to share any of your helpful wingmanship techniques, feel free to write us at: academy@stylelife.com and we may just feature the technique on our blog.

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