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To be "on the train of despair" means to be single and in pursuit of someone to spend the day and/or night, without the intent of perusing a relationship with that person.

On Valentine's Day the only way to "get off the train" would be to find a date, to give up in the pursuit of finding a date or when the clock strikes midnight and you're all alone.

Related: To be on the desperation train / To be on the train of despair / To be riding the train / To be on the train / To be off the train.
- What are your plans for V-day?
- I'm on the train of despair this year.
- No worries dude, you'll be off the train way before V-day.
by a66spam February 01, 2014
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