The Chicago Guide to Dating Volume I - How to Find a Date

Good places to talk to strangers

• The laundromat – If you see a cute girl/guy at the laundromat, strike up a conversation. Both of you are there waiting for your laundry, so why not make a friend during the spin cycle?

• The grocery store – People often grocery shop alone and they are generally not in a huge hurry. So roll your cart up next to your stranger-of-choice and ask them their thoughts on the current sale on Captain Crunch. Or if you’re a boy, tell the girl that you’re making dinner for your mom and you are in need of some suggestions on what to make. She will think you are adorable because a.) you cook and b.) you love your mom. Score!

• A coffee shop – I couldn’t tell you how many times I’ve had strangers strike up conversations with me at coffee shops. You have to be careful though, because some people are actually trying to work or study and you don’t want to bother them. Look for people browsing facebook. They are clearly not very busy.

• The El – You have to be quick with this one, because you don’t know how many stops you have before the person gets off and is gone forever. Think of it as a ticking time bomb. You see an attractive girl/guy. Sit/stand next to them if possible. Comment on how much you hate the CTA. See if they take the bait. If they do, talk as fast as you can and make them laugh. You probably won’t have time to exchange numbers, so hand them a business card right as they are getting off at their stop. Unless they call, you’ll never see them again so you have no reason to feel like an idiot.

• The bar – This is a no-brainer. If you don’t already talk to strangers at the bar, then I don’t know why you go in the first place. Everyone goes to the bar to talk to strangers. When alcohol is involved, you should lose all your inhibitions. Just start talking! If it’s going well, buy yourself some time by offering to buy a round.

• The beach – This is simple. Go up to someone who looks nice and ask them if they’d like to join you in a game of beach volleyball. If they find you attractive, they will say yes. Everyone goes to the beach to have fun and relax, so you shouldn’t feel weird about approaching new people. Just be careful not to hang around too long with people who doesn’t seem interested. You’ll come off as desperate.

Talking leads to flirting

Great, so you’re talking to more strangers. Good for you. Just try not to get discouraged if every random person you talk to isn’t interested in dating you. But if a conversation is creating a lot of smiles and laughter, start flirting! Flirt your heart out…. flirt like you’ve never flirted before. This is your only chance at making a good first impression, and if you want that person’s number then you’re going to have to show them you’re interested.

Speed Dating and Singles Mixers

Okay, so some people will never be good at talking to strangers. That’s okay. You have some other options. First of all, speed dating. You pay a small fee ($20 or so) to meet 10-15 members of the opposite sex in an hour or two. You write down the people you felt a connection with. If they write down your name too, you both will be notified. Then you can set up a real date and get to know each other! (Okay, so I think that is how it works… I’ve never actually tried speed dating, but I know people who have.)

Another option is to attend a singles mixer. (Which I also haven’t tried.) There are some companies right here in Chicago that sponsor these types of events and you should check them out if nothing else is working. You will have the comfort of knowing that everyone else there is single and looking, so you’re not alone.

Try online dating

If you’re on here reading my guide for advice, chances are that you’ve already tried online dating. But if you haven’t, maybe you should. Millions of people have signed up for an online dating site, and thousands more jump on the bandwagon every day. It’s a growing trend to meet your significant other online—just ask anyone in the wedding industry.

I know there is still a stigma associated with online dating… many people feel that only desperate people do it. But if you ask me, you have a way better chance meeting someone online then you do sitting at home watching TV. Why not give it a try? Here’s a list of sites to check out first.