Hooking up with a large number of new sexual partners in rapid succession.
Tim: So I saw three new girls this week
John: You're getting back on the strange train aren't you?
Tim: Well I don't plan on stopping for a bit, so yeah.
by Timq89 November 21, 2014
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Sex outside of your current relationship while traveling via train.
While aboard the Amtrak #22 North bound for Poplar Bluff Missouri I decided to go hit the bar car in search of some train strange.
by K to tha G beotch October 16, 2019
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When someone has no self respect or standards and solely hooks up with a string of women he does not know or care to know. Generally a douche bag.
Friend 1, "Man, Jeff sure has been hooking up with a lot of random woman"
Friend 2, "yea, he has really been riding the strange train lately"

"Fucking guy has been on the strange train for a solid month now.

"Wow, he really jumped back on the strange train after his break-up"
by Texas Blouses January 8, 2014
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