ride the wagon

to take the initiative.
to make the first start.
to lead.

a guy should not wait for a girl to propose him.
he should be smart enough to ride the wagon

a guy should ride the wagon in a relationship.

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riding the covered wagon

The uncicumcised penis closley resemble a conastoga wagon or "covered wagon"

Thus this is a term used by females that engage in top mount intercourse with a male that is uncircumcised.

What you doing tonight Sue?

I'm riding the covered wagon!

Ewww, T.M.I.

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Riding The Singularity Wagon

My way of saying, "I'm Single". That's all.

Inspired by the teetotaling phrase "Riding the Water Wagon".

If you're riding this wagon, you're all alone.

"How come Jesse has a girl, but I'm stuck riding the singularity wagon? What the actual f*ck?"