The Professional Wingman: How to pickup people on Boston's MBTA - Metro US

The Professional Wingman: How to pickup people on Boston’s MBTA

For some people, it is difficult to approach an individual while in public that you find particularly attractive.

When it comes to doing it on public transit, it is even harder. With so many people around packed–in tight, listening to every word you have to say, and most likely Tweeting about it and making fun of you…it’s too much pressure and way too much room for embarrassment.

But a Boston-based “wingman” business has some tips to help you get over your fear, and talk to that T crush you might have.

Here is what “the Professional Wingman” has to say about approaching those pretty ladies (or handsome gentlemen) on your MBTA ride:


-Most people travel alone. Unlike a bar, you don’t have to worry about other people vying for their attention and distracting them. In fact, there’s a chance they are bored and are in this “unknown void” of getting from point A to B.

-Most people aren’t on the phone when waiting for or on the train. Typically when people are above ground, they’ll most likely be on their phone. Being underground gets rid of that. One less distraction for you to deal with.

-Most people aren’t moving around. Besides the bar, public transportation is the only place where people aren’t really moving around.

Use the 3 C’s: Context, Confidence and Content.

Context: Find opportunities to be near them. On public transportation, the goal is to stand (if they’re standing) or sit (if they’re sitting) next to them. Never put yourself in a position where only one of you is sitting or standing. It’ll be uncomfortable for both of you.

If you can help it, talk to them before getting on the train so it gives you more time to build that rapport since you may not know how much time you’ll have.

Confidence: The most important thing you can do is talk to other people prior to approaching that person. Ask people questions before getting to the station. If you stop by a coffee shop before hitting the subway, talk up the barista. The goal is to get you in a chatty mood and socially warmed up.

Content: Be direct, but not too direct. I would STILL recommend saying the usual, “Hi…” However, because it’ll be quiet, you don’t want to be overt about meeting people — to avoid the creep factor.

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