Stef is "Chicago’s Introductionista”, and the owner of Stef and the CityShe is a matchmaking and dating expert in Chicago, and has been in the business for over 12 years,

Stef Safran

Stef Safran

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5 great date ideas for Halloween weekend

5 great date ideas for Halloween weekend

Halloween weekend is around the corner. While it's a great time of year to go out and party with friends, it's also an opportunity to spice things up with your significant other. And living in Chicago means you have seemingly endless options for you and your partner to get into the spirit. Bond over your love of all things spooky this Halloween with these five date ideas. Check out a haunted house: If you're brave enough, tons of haunted houses in Chicago and the surrounding suburbs offer up a good scare. Getting spooked gives you the chance to cuddle up. Plus, you’ll have the opportunity to see whether your date is a wimp. Think a haunted house is a bad idea for a first date? One study shows an adrenaline response (like the one we get when we’re scared) actually strengthens attraction. When our hearts speed up, our bodies don’t always differentiate between fear, nerves, love and so on.  Wander through a corn maze: Everyone knows Illinois is full of corn. Why not get lost in it? Taking a date to a corn maze is a great opportunity to work together to find the way out. If a regular corn maze isn’t for you, try a haunted one that's only open after dark. Get weird at a costume party: This one's easy. Have some fun together at a costume party. If you're not afraid of being cheesy, collaborating on couple's costumes can be downright adorable. If your idea is super creative, think about entering one of the many costume contests around town. Or, if you're not sure what you'll talk ab
4 reasons why you should get into a relationship in Chicago this fall

4 reasons why you should get into a relationship in Chicago this fall

The warm weather is slowly fading in Chicago, and most people will soon get the urge to stay inside and wait out winter alone after their summer flings fizzle out. That line of thinking, though common, is counterproductive for a single person on the prowl since autumn is the best time to get into a new relationship. Here’s why you shouldn't stay single in the city this fall. It's the real season of love: After all the little loves found during summer, most people are ready to get serious about finding a partner by fall. The fact that Chicago winters are a harsh time to spend alone doesn’t hurt either, making people especially more prone to "wife up" in preparation for winter. A recent Facebook survey shows more people get together in the fall and stay together long-term than any other season. The largest number of engagements also happen in autumn. Fall is the perfect time to get yourself out there for more than a passing romance. There are innumerable date options: From apple picking to pumpkin carving, fall has some of the best date ideas for the entire year. A countless number of festivals can be found across the city, and pumpkin patches pop up all around the surrounding suburbs. Finding a special someone means you always have a person to enjoy these seasonal activities with. It's finally cool enough to cuddle: There’s always an excuse to snuggle up in the fall, especially with a new beau. You can put on a scary movie and cuddle up or decide to get a little closer while f
5 reasons you should be joining a sports league in Chicago this summer

5 reasons you should be joining a sports league in Chicago this summer

When you're trying to meet new people, it helps to put yourself in settings where you don’t have to make friends in a single two-hour event. A large city can become so overwhelming, and structuring your time so that you have an automatic “social hour” with a sports league can be great for your social life, particularly if you are in your 20s and a lot of your friends are coupled up. Not convinced yet? Let’s go over some reasons why joining a sports league is something you SHOULD do this summer. 1. It’s a tradition in Chicago: Softball and beach volleyball are both traditions in Chicago. With hundreds of teams to choose from, someone you know will probably be joining a league (or leagues). In addition, Chicago is the nexus of 16-inch softball, which is not really found anywhere else. 2. It’s a good way to meet people without breaking the bank: How much do you spend when you go out for dinner or to a bar? Probably too much. A sports league basically runs you about $10 per game (plus your bar bill afterwards), so it’s a cheap and easy way to meet people, and it can easily be a whole-evening activity. 3. It’s not that competitive: I’ve heard this one a lot: “But I’m not good at it!” There are competitive leagues out there, but many of the co-ed softball, volleyball and kickball leagues are purely for fun. I have yet to hear someone tell me that their volleyball or kickball team was too good. While softball may be a bit trickier, we have the “16-inch mush ball," so that's another
5 things that make you undateable in Chicago

5 things that make you undateable in Chicago

The new NBC show Undateable makes for a cute comedy, but in real life there are way too many people who make themselves “undateable." Unlike the TV show, they refuse to listen to their friends' advice, and fail to change. While the show takes place in Detroit, Chicagoans also have a lot of things that can make them “undateable.” 1. You live in the suburbs: If you live in the suburbs during your 20s, you probably have been told that “it’s not cool." For many 20-somethings, what it really means is that living in the city is something that you might only do once, before all of the responsibilities such as mortgages and children come into the picture. For many, living in the suburbs hints at being too close to mom and dad, or the inability to be able to handle change. 2. You refuse to try anything out of your usual neighborhood: If you do live downtown and you tell someone that you don’t know of anything to do that isn’t within a few blocks of your work or home, it won't set well. I actually had one woman tell me that even though she lived in the city, she didn’t know how to take public transportation and didn’t plan on learning. 3. You refuse to change your look: The Goldbergs should not be the inspiration for how you still present yourself. Your wardrobe, your hair and appearance make a difference. Chicago is a trendy city, so make sure that you are willing to update your look if your friends and family keep telling you that it's out of touch.  4. You refuse to dress up for dat