Going out alone vs with a wingman
A wingman makes it easier to go out. Going alone makes it easier to approach. That's the trade-off in one line, and most people end up doing both depending on the night.
If you're deciding which to try, here's what each actually gives you, what each costs, and how to make a wingman setup work without it turning into two guys standing by the bar daring each other.
What a wingman is for
In pickup slang, a "wing" or wingman is a friend who goes out with you to meet people. The old pickup idea of a wingman was partly tactical: someone to "handle" the friends of the person you're talking to. Flow doesn't recommend that framing. Friends looking out for each other aren't obstacles to be managed.
A good wingman is simpler than that. He's a friend who's also trying to get better at meeting people, and who makes it more likely you'll both actually do it.
The case for going with a wingman
Accountability. It's easy to bail on a plan you made with yourself. It's much harder to text a friend "actually I'm staying in." And once you're out, it's harder to spend the whole night not approaching when someone's watching.
Momentum. Seeing your friend approach someone and survive makes your own next approach feel more possible. Some nights you'll carry him. Some nights he'll carry you.
Feedback. A friend watching from a few feet away sees things you can't. You stepped back right after saying hello. You talked twice as fast as normal. You looked at the floor when you asked for her number. That's hard to learn any other way.
It looks normal. Two friends out together don't draw attention. Standing alone at a busy bar can feel conspicuous, especially when you're new to this.
Company between approaches. A night out is a lot of waiting. Having someone to talk to keeps your energy up and makes rejection easier to shrug off.
Safety. Someone knows where you are, and you can keep an eye out for each other.
The downsides of a wingman
Dependence. If you only approach when your wing is there, you haven't really learned to approach. You've learned to approach with a safety net.
Waiting on each other. One of you wants to leave, the other is mid-conversation. One is warmed up, the other is still nervous. Coordinating two people's nights takes effort.
The wrong wingman makes it worse. Someone who gets too drunk, mocks you after a rejection, competes with you for the same person, or pushes you to stay in conversations that aren't going well is worse than no wingman.
Talking instead of approaching. It's very easy to spend three hours chatting with your friend about approaching and never approach anyone.
The case for going alone
No excuses. There's nobody to talk to except the people you're there to meet. That pressure is uncomfortable and very effective.
You're more approachable. A single person is often easier to start a conversation with, and easier for others to start one with you. People who'd never walk up to two guys might chat with one.
You can follow your own pace. Leave when you want, stay when it's going well, change venue on a whim.
It's better for the day. A lot of day game happens on your own anyway: a cafe, a bookshop, a walk through a market. You don't need anyone with you to say hi to someone in a queue.
It builds the real skill. Approaching on your own, without anyone watching, is the clearest sign that the nerves don't run the show anymore.
The downsides of going alone
Harder to start. The first approach of the night is the hardest, and alone, nobody's nudging you.
It can feel lonely. A string of rejections with nobody to laugh about them with can end your night early.
No feedback. You'll have to rely on memory and notes. A field report helps a lot here.
Some venues feel awkward solo. A loud club is harder to navigate alone than a coffee shop.
Side by side
| With a wingman | Alone | |
|---|---|---|
| Getting out the door | Easier | Harder |
| First approach | Easier, with encouragement | Harder |
| Approaches per hour | Often fewer (more chatting) | Often more |
| Feedback | Live, from someone watching | Only your own notes |
| Approachability | Two guys can seem like a unit | One person seems more open |
| Best for | Night game, new venues, early on | Day game, building independence |
How to pick a good wingman
Look for someone who:
- Wants the same thing. A friend who's also working on approaching, not someone who just wants a night out drinking.
- Is supportive after rejection. Laughs with you, not at you. "Good approach, she just wasn't feeling it" is the right energy.
- Is respectful. If he's dismissive or crude about people, or pressures anyone, he'll make your night worse and reflect badly on you.
- Is roughly as committed as you. If one of you wants six approaches and the other wants one, you'll both be frustrated.
Ground rules that help
Agree on these before you head out:
- Set approach goals. "Three each before 11" gives you something concrete to hold each other to.
- No standing still too long. If you've been chatting by the bar for fifteen minutes, one of you goes next.
- Don't compete. If you both notice the same person, whoever spotted them first goes.
- Respect a no for both of you. If someone isn't interested, you both leave politely. Never pressure a friend to "go back in" after a clear no, and never pressure the person. See consent and respect in cold approach.
- Include, don't split. If your friend approaches a group, you can join in and be friendly with everyone. Don't try to peel people away from each other. More in approaching someone who's with friends.
- Agree on leaving. Whether you leave together, separately, or check in by text.
- Debrief afterward. Five minutes on the way home: one thing that went well, one thing to try next time.
A middle path
You don't have to choose forever. Lots of people go out with a wingman, warm up together, then split up for an hour to approach solo before meeting back up. You get the accountability of a plan and the independence of going alone.
Another good pattern: wingman nights for night game and new venues, solo for day game and low-key practice.
If your friends aren't into this, Flow has Wingman, where you can post a plan to go out and see others' plans within 5 to 50 miles. It's an easy way to find someone working on the same thing, and the weekly friends scoreboard keeps you both honest about actually approaching.