#1: I pulled out of MickyD’s after picking up the 2 Cheeseburger value meal, because I was hungry but wanted something very quick.

Barely a block away, I’d eaten CB#1 and decided that 1 of these things hitting my gut is enough. At a stoplight, a woman is going car to car, begging for some money for some food. I hand her a Micky D’s bag, with a fresh, hot, cheeseburger inside, briefly explaining what it was. She gave me a dirty look and started to walk away, then reached back and grabbed the bag. I think the crackhead wanted $1 towards her next fix, and didn’t care about eating.

#2: On my way into a divey bar, a young, somewhat disheveled guy asks for “$2.75 for the bus to Framingham”. I wasn’t feeling very generous at that time & place, so I declined his offer. 5 minutes later, in the bar, the same guy walks in and drops a pile of change on the bar, orders a Schlitz, and starts counting out his money. Looking up behind the bar, what do I see? Schlitz on special for, you guessed it, $2.75.

#3: Outside a convenience store, adjacent to a housing project an older lady hits me up for money for a sandwich for her child. I won’t give you money, I tell her, but I’ll buy a sandwich in the store. We go in and she picks out one of the sandwiches from the cooler. I head for the counter, and she asks, “what about a drink”. Starting to feel I’m being played, I grab a $0.99 bottle of water. She points to a $2.99 bottle of Iced Tea. I say, “absolutely not”. She gets mad. I pay the clerk and stop talking to the woman. Clerk rolls his eyes and says she’s a nut, and I shouldn’t encourage her…

The only person I’ve given to in a while is a guy who, when he asked for money, I asked him if it was for booze (we were near a liquor store). He said yes, and instead of $1, I gave him $5.

Cheers, dude.

and then someone drew a cartoon about him in the student newspaper that depicted him having a radio, ipod, bmw, and other things… and i was incensed somebody would think he was “conning” college students (he was never begging for money, merely keeping warm), but it definitely altered the way i thought about him from then on. sadly, i never found out if he truly was homeless…

also, re: umbrellas — they are pretty useless in boston because of the wind (it’s hardly ever rainy and NOT windy). i’d suggest investing in one that comes with a replacement warranty (kind of like how l.l. bean does with their backpacks and such), because you will go through SO many. either that or invest in a rain jacket with a hood.