I wish I could do this. Too bad the Mass Pike doesn’t have a set toll amount. My end of the state is free too so it’s possible the person behind me doesn’t have to pay anyway. But, if they get on in Boston, it could cost upwards of $5 for them and I’d never know it. I’d especially like to do it just because I never have pay. I’ll be sure to do it the next time I pass a toll bridge though.
I’ve never had anyone do a random act of kindness for me but it’s ok. I prefer giving it out.
No toll roads where I live. But I do the same thing every now and then at the gas pumps. See someone who looks down to their last dime, swipe my card at their pump, smile, and say fill’er up… it’s on me.
If I’m eating a meal in civvies and notice an enlisted person in uniform eating, or a small group of them together, I’ll occasionally ask the waitress if she can help me pay for their meal anonymously. I’ve been successful twice and failed once; the secret is to overpay ahead of time (in case they get refills or dessert or tip small) and leave. I’ve had my meal paid for while in uniform – that’s where I got the idea.
I also left a twenty at a toll booth on the Chesapeake Bay Bridge and told the lady to “keep waving 'em through until it’s used up, and enjoy your break.” I’ve been waved through two toll booths since.
I also approach strangers in bookstores who are thumbing through Ender’s Game indecisively and offer to purchase it for them if they’re not sure, on the condition that if they like it, they buy their own copy and give theirs to a friend. Mr. Card signed my copy “thanks for finding new readers for my stories!”
The toll booth the OP mentioned is a mess because there are two curves right before the approach, and anyone with poor following distance will be caught by surprise. Instead of a casual slowing, un-merging, and stopping, you get a stop-and-go gridlock pattern and a huge line of cars.
Ah! Right – it’s exasperating for me, cos my exit is the first one in DE, and that’s how to get home to my mum’s house since 1981, so as you can imagine, driving for 6 hours on the interstate and then getting stuck so close to home makes me stroppy.