NeedThisSoon / September 23, 2005 2:29 PM

At this point of my singledom, nothing sounds better than a couple of bottles of two buck chuck, late afternoon going into evening by the lake....and if was the beginning of the relationship I'd blame too much wine for sleeping with them, if it was later, I'd just admit I love me some tipsy sex.

Steve / September 23, 2005 2:52 PM

Take her to the OTB and bet on a long shot.

If I win, she knows I'm a lucky star and we go out to a fab dinner.

If I lose, then at least I'm a hopeless romantic/dreamer, and chicks dig them, right? So then we could go window shopping or something.

e_five / September 23, 2005 2:52 PM

Start lookin' for crack whores!

what the / September 23, 2005 2:56 PM

A bottle of boones farm and 2 tickets on the last run of the night on the purple line.

anne / September 23, 2005 3:04 PM

First Fridays are good sources of free booze, and they happen in galleries all over town (in two weekends, in fact).

I like late nights in coffee shops too.

jennifer / September 23, 2005 3:58 PM

bring my scrabble board to a coffee shop and hunker down for some serious triple word score action over a few lattes.

Baltimore / September 23, 2005 4:06 PM

hummmm.. Nice crisp fall eve drink'n wisky in Humbolt Park or on a bench in Logan Square Blvd doing a lil of the same. Oh I do that by my damn-e all the time

punk / September 23, 2005 4:08 PM

Go to gibson's and order a $100 bottle of wine, the biggest steak on the menu then do the old Dine and Dash.

Leelah / September 23, 2005 4:21 PM

Given my recent dating history, I'd probably be paying the guy $10 just for taking me out.

waleeta / September 23, 2005 4:41 PM

Brew and View and hopefully some kissing.

laura / September 23, 2005 6:03 PM

that's easy! dinner at my place. my kitchen is usually stocked well enough, so 10 bucks would easily cover the last minute fresh produce. on the off chance that my bar isn't stocked well enough, i'd scratch the produce and spring for booze.

and my cat is so stinking pretty, that if i can't win her over with my wit, charm and mad cooking skills, kitty will steal her heart faster than she can say "what's that smell?".

Moon / September 23, 2005 9:40 PM

Buy a quart of Jack and stay home???

jennifer, I would SOOOO kick your ass at Scrabble!

PMan / September 23, 2005 10:59 PM

Six pack and a joint at Ardmore beach is one of my favorites.

Moon / September 24, 2005 10:10 AM

Take her to the OTB and bet on a long shot.

If I win, she knows I'm a lucky star and we go out to a fab dinner.

If I lose, then at least I'm a hopeless romantic/dreamer, and chicks dig them, right? So then we could go window shopping or something.

Yeah, that'll work. :Rolleyes:

Because the OTB is such a classy joint. Hee hee. The first horseplayer she sees will cause her to run out screaming.

/Horseplayer
/I'm disgusted by some of those guys

Billy Ray Valentine / September 24, 2005 10:25 AM

Moon, where can you buy a quart of Jack for $10?

Ron / September 24, 2005 10:26 AM

If you happen to own a pair of Zubaz, you'll feel right at home at an OTB.

Moon / September 25, 2005 11:59 AM

Zubaz might be a little hip for the OTB crowd, but I have seen them. Mostly it's raggedy ass clothes with food stains.

Maybe I should have said a pint of Jack (geez, when did that get so expensive???)

Mary Washington / September 25, 2005 12:39 PM

I'd buy Condoms.

mike / September 25, 2005 1:46 PM

Fill up my gas tank (as much as possible) and drive to the Mississippi river to watch the river boats on a pier.

Mac / September 25, 2005 4:23 PM

Ask her to pay ;-)

Actually, an afternoon coffee and walk around Lincoln Square talking joking flirting hand-holding.

Erica / September 25, 2005 10:27 PM

The real bang for your buck, though, is the Mutiny (free live music) and two mini kegs of beer ($5 a piece).

Tues. night movies at AMC ($5 gets each person in a movie and a small bag o popcorn). Smuggle in yr own candy and soda.

I second making your own romantic dinner.

When I lived in Lakeview East, we used to take the smoky joe down to Belmont Harbor and cook out.

You can get two pretty darn wonderful sundaes at Margie's for $10 or under w/tip.

Nothing beats getting to know each other over a cup o'joe at a diner. You could slip dessert in there somewhere, too.

printdude / September 26, 2005 6:56 AM

Spend six bucks at Issacson & Steins on fish.
Take it home and whip up some fantastic meal, tell my date to bring the wine.
Spend the other four bucks on a rental movie of classic proportions like "the Thin Man", or "the Maltese Falcon" and let the cuddling begin!

Moon / September 26, 2005 8:30 AM

You'd be better off with a Cary Grant movie, printdude.

Trust me on this one.

holden / September 26, 2005 8:50 AM

Check out the free pass to the Art Institute from CPL, trade some thoughts and critiques on the incredible masterpieces there. then, either walk to the lakefront to sit on the rocks and watch the boats or walk up michigan ave for some windowshopping. grab a couple 40's for the ride on the blue line home.

Erica - great call on the Mutiny!

holden / September 26, 2005 8:56 AM

throw on your favorite team's jersey and head to Ginger's Ale House early on a Saturday to take in a Premiership match and sip Coke's.

Jeigh / September 26, 2005 9:06 AM

Take that ten bucks and go shopping at Whole Foods, then come home and begin preparing the all wonderful food we purchased. My date and I will each get one bite a piece... Then we'd go out to eat and forget about this ten buck limit nonsense.

C-Note / September 26, 2005 9:43 AM

You can get a fifth of Jim Beam for $10 at Dominick's.

Baltimore / September 26, 2005 9:57 AM

Go see the Rastas down on Lenox Ave for dat early bird two for ten dolla ready rock special and then its all bout that beam me up Scottie for the next 20 minutes! And after that we pan handle for a couple ah hours and the cycle starts all over again! Man I miss New York

Kevin / September 26, 2005 10:49 AM

I'm surprised nobody has mentioned North Avenue at 1:30am. For a sawbuck, you can get exactly what you want and be on your way back home by 1:35am.

Moon / September 26, 2005 11:11 AM

You can get a fifth of Jim Beam for $10 at Dominick's.

It's just not the same, C-Note. It's just not the same. :D

Ray / September 26, 2005 11:23 AM

It sounds like a pilgrimage to Margies Candies would be in order.

MikeH / September 26, 2005 12:41 PM

I can't believe no one has said Lincoln Park Zoo. Many a "lucky" female has been on the receiving end of the famous "Mike Zoo Date."

MikeH / September 26, 2005 12:42 PM

Just realized it said date "night." No matter...we'll just have to sneak around I guess, and since the food vendors will all be closed, he'll spend the ten bucks on a bottle or two of wine...

Veronica / September 26, 2005 1:06 PM

Well, I don't really like "dating," per se, but if I had $10 and I were with someone of the male, heterosexual variety who had expressed his interest in me, as I had in him, and we wanted to hang out together on a random night, I'd say coffee and a shared dessert would be a great thing to do. As long as I can wear jeans and sneakers, I'm cool.

HuckleCat / September 26, 2005 1:47 PM

Great suggestions, Erica.

I personally enjoy a stroll through Graceland Cemetery.

madachode / September 26, 2005 2:01 PM

10$, a windshield wiper to give the date a good thrashing with.

Hambone Deluxo / September 26, 2005 3:51 PM

A boatride to my private island where I'll show her how to hunt the most dangerous game with... wait how many bullets do 10$ buy again

Moon / September 26, 2005 3:52 PM

I'm a bit worried about MikeH. I think he may be breaking into the monkey house after hours and doing God only knows what to the female monkeys.

:D

Rebecca / September 28, 2005 1:42 PM

I second scrabble.

booze + scrabble + scrabble-related-trash-talking = one hell of a $10 date

Kim Siever / September 28, 2005 2:01 PM

My wife and I did this very thing.

We each had five dollars and had 30 minutes to see who could by the most things with her/his five dollars. Another part of the contest was to see who could get the closest to using all of the five dollars.