5 Benefits of Dating in Chicago During COVID

benefits of dating during COVID in chicago - windy city cosmo

As if there weren’t enough obstacles to finding the one, let’s add a pandemic. But said pandemic actually helped me find a boyfriend for the first time in my life.

I’d be lying if I said I wasn’t enjoying dating during COVID. Naturally, with challenges comes creativity. I’d make plans and then we’d both show up at a restaurant that was closed or booked. We’ve met at a poorly lit patio with no heaters. We’d try to find a place and then just end up sitting on a park bench drinking a Truly.

All of those things actually happened. But, from a girl who has actively dated in Chicago for most of her adult life, I wanted to share something positive that came out of COVID, and that would be my dating life. Time even reported that there was a rise of “intentional dating” due to the pandemic. 

I want to preface this by saying, I didn’t immediately start dating during COVID. I actually used the first month or two to write articles for Windy City Cosmo, run a 5K a day, and tried new things like becoming vegan for a week and doing paint by numbers.

I enjoyed using this time to talk to family and friends and really work on myself. But, I also really want to find my life partner. It’s an important part of life to me. So, at the end of May, I started talking to one guy and we actually met up during a protest. I will share this story – how I got my first boyfriend during a pandemic – in a later post.

But, I wanted to share with you some positives about dating right now during COVID. I think right now, has quite honestly been my best dating experience. And it’s not because I’ve fallen in love. I’m just finally enjoying dating.

You Actually Get to Meetup During Normal Hours

I know this sounds weird, but it’s true. Since having a curfew, it makes it really easy to go out. I don’t care to go out past 8 or 9 pm, especially during the fall and winter when it gets darker out. Now that everything is pretty much shut down at 10 pm, and there was a time I think the curfew was 8 or 9 pm, it made it easier to have a normal date – you know, one where you meet up for an hour or two and go home.

Since quarantine, I haven’t had a guy invite me to his place as a first date. And that in itself is one of the nicest things. I feel more respected that a guy has normal hours for me in his life and I’m not just an afterthought at 11 pm after he’s tipsy or been out all night. Call it what you want – but I think it’s really attractive that from the start, we’re actually making time for each other and it’s not just on to the next event or next date. It’s that this is the thing we are doing tonight – we’re going out.


Dates are Simpler, But More Romantic

Okay so finding a place to go on a date in Chicago was frustrating at times. It felt like every restaurant was booked or I’ve gone on dates and it was pouring rain. But it kindof worked somehow. There’s something romantic about meeting up and going for a walk in our neighborhood and grabbing a coffee. It made it more comfortable and easier to get to know.

I also loved that we picked one place to go. So, we didn’t feel like we were rushing off somewhere. We could sit and relax and enjoy the view and each other.

Also, because places got booked, you usually had to make a reservation. So, it’s just like the little extra effort. It made dating more romantic to have reservations at 7.

You Get to Know Someone Before Going Out With Them

Weird, right? With dating apps, there was a tendency to meet someone that night or that weekend. Everything happened so quickly. Now, I’ve actually gone weeks talking to a guy before meeting up with him. I got to know his views on religion or healthcare and get more in-depth then a superficial profile. I stopped meeting up with people as if they were just something to do on a Friday. I started to get to know them and actually be excited to meet them (and let’s be real, get out of the house).

I miss this part of dating – actually getting to know someone and liking them beyond a moment or a feeling.


It’s Easier to See a Guy’s Character

Like I said, I’m really impressed that no guy has asked me to come over during COVID. Ok, let me be 100% honest – no new guy – has asked me to meet up at his place during COVID.

During a pandemic, there’s a lot of fears and concerns. It’s risky to meet someone new and go out. Everyone has their level of comfort. Some people don’t like going to a restaurant other’s just want to sit on a patio. Some people want to keep their masks on and just go for a walk. For me, I’ve tried to take public transit as little as possible. So, I’d only want to go places that I could walk to and of course, that meant during normal hours since I’m not walking home at midnight.

Being in this setting has really shown me how caring and kind and thoughtful guys are. A bunch of guys walked me home and I think only one or two asked to come in. I somehow dated a lot of guys with cars so they drove to my neighborhood or picked me up. And it went beyond that. One guy switched seats with my halfways during our date so I could be warmer next to the heater. It’s just really nice to be around gentlemen.


You Don’t Feel Pressured to Move Too Fast

I tend to have dates that go from brunch till midnight. I don’t know how it happens – but when I’m vibing with someone, we just keep exploring and going. The problem is that we feel like we’ve know each other forever and by the end of the date, he practically wants me to sleep over. I like going back to this way  – when I know we’re meeting at 6 and I’ll be home by 8 or 9 pm. It takes a lot of the pressure off.

Also, I know you’re not supposed to kiss and tell, but I like those guys who didn’t try to kiss me on the first date or make me feel uncomfortable. It’s risky to kiss someone during COVID. You don’t know if they have it or who they’ve been around. This can feel a bit awkward at first because affection is nice. But I liked that we could just figure out the basics – like do I actually like the person sitting next to me – instead of feeling pressured to kiss a guy, who probably won’t remember my name (and yes, I’ve had guys during quarantine try to talk to me and they forgot that we went out already).

Final Thoughts

Am I closer to finding love? At the time that I originally wrote this, I thought “probably not.” I won’t lie and say that I’ve liked every guy I’ve dated during COVID. I’ve definitely walked out of a restaurant.

Dating is difficult right now. But I will tell you that I feel more respected dating now, and I guess, more importantly, I respect myself more. I feel like what we were doing before – or what I was doing – was being around guys who just viewed me as a hookup. And even if that’s their end goal now, I know it before it goes further.

I am happy to report that after writing this and being persistent with dating, I did start a relationship and it is going very well. So, I hope this leaves you with the hope to carry on and find the one. 

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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