For someone who loves to travel, it’s especially thrilling to share that your latest trip resulted in getting engaged. And that’s just what happened during my trip to Midwest for the holidays.

After spending last Christmas in LA, Tyler and I planned to visit our respective homes for the holidays. I’m from Grand Rapids, and he’s from Chicago - two cities that are roughly a 3-hour drive from each other. This meant that visiting our families in one trip is a pretty easy endeavor. 

Our Christmas vacation didn’t exactly start as planned though. A family emergency forced me to travel more than a week earlier than I was supposed to. Despite a scary close call, everything turned out okay. Though I was in and out of the hospital, I was still able to show Tyler around town. I took him to the Grand Rapids Public Museum, ice skating, downtown, and had him meet some family and friends. 

After Christmas, it was time to head to Chicago to see Tyler’s family. He showed me where he grew up, went to school, used to work, and more. He even took me to see the Home Alone house! Fun fact: the Home Alone house is in Winnetka, just outside Chicago. 

Though we spent the majority of the week in the suburbs, we had planned to spend New Year’s Eve in the city. Tyler booked a reservation at the Drake Hotel. This hotel is a famous hotel in Chicago and is absolutely gorgeous inside. The name ‘Drake’ is also a Seinfeld reference, and since Tyler and I are both fans of the show, it was a perfect fit for our big NYE in the city.

We arrived in the city in the late morning, first heading to the Christkindlmarket at Wrigleyville Stadium. While the main market location at Daley Plaza had already closed for the season, the Wrigleyville one was still open. It was smaller than we thought it would be but still cute to see. They had ice skating, a massive Christmas tree, and vendors selling food, over-priced hot drinks, and winter accessories. We chatted with Tyler’s friend Johnny for a bit and then left the market to go check in at the Drake.

Being in Chicago around the holidays - and especially staying at a hotel like the Drake - felt like my own version of Home Alone 2 when Kevin stays at the Plaza Hotel. The Drake was busy too, as the hotel was hosting a fancy New Year’s Eve party later that night. 

After check-in, we both got ready for dinner and then headed out. We wanted to go somewhere that felt special to Chicago and was close to our hotel. We decided on Harry Caray’s 7th Inning Stretch, a cool sports bar and restaurant in the Water Tower Plaza. We had made a 5:45 reservation, but we were both really hungry so we decided to see if we could get seated earlier. It was a good thing we did because we had no idea the restaurant was closing at 6! We still had enough time for a nice dinner though. Tyler ordered a veggie burger, I ordered a chicken Caesar salad, and we both got a beer. 

During dinner, though, Tyler began tearing up a bit. My natural instinct was that something was wrong and he was worried about other things going on at the time. I would shortly learn, though, that the sentimental tone was for an entirely different reason. 

Once we finished our meals, we went to the nearby Hancock Building to see if we could look at some high-top views of the city. I had previously gone into the Hancock on St. Patrick’s Day in 2019 to catch the views during the day. Fun fact: the women’s restroom at the Hancock has the best views of the city and lakeshore. Unfortunately for us, the Hancock decided to close all their windows so you couldn't look out. Not sure why they did this on NYE of all nights, but nevertheless, it was a bit of a bummer. 

We continued to walk along the Chicago streets near our hotel, taking in all the beautiful Christmas lights on display. Seriously, Chicago may be very cold this time of year, but it’s absolutely stunning with the Christmas lights. I would absolutely recommend seeing Chicago during the holiday season in a heartbeat.

At one point, Tyler suggested crossing the street to where the historic Chicago Water Tower was located. I remember seeing this before when I visited in 2019 and thought it was very beautiful. It’s a water tower that looks more like a historic church or small castle. 

I walked up to the Water Tower with Tyler, noticing all the Christmas lights surrounding it and complementing how romantic it looked. As we walked alongside the tower, Tyler began telling me its history and then spoke about our relationship and that he wanted more. It was then that he got down on one knee and said “Jill Marie Zwarensteyn, will you marry me?”. I just remember being in a state of happiness and shock as my hands were over my mouth. I was smiling, crying, and I kept trying to get out a ‘yes’ - though I know for sure I was able to manage a head nod. It’s funny how these moments almost feel like a dream. 

The proposal was incredible though! And the Christmas lights all around made it perfectly romantic. For any  fellas who want to pop the question, I'd say the Water Tower at Christmas is one of the best places to propose in Chicago.

Tyler then got up and placed the ring on my finger. Shortly after, a cop came over and said to us “I saw the whole thing. I hope you said yes. Would you like me to take a picture?”. We were very grateful since we didn’t have anything else with us at the time to take photos.  

The first people we called were our parents. My mom said she had a gut feeling she knew what my good news was. Moms always have a way of knowing that stuff.

After getting off the phone with our parents, a couple of girls came over and asked us if we wanted them to take a video of us reenacting the engagement. Now, here me out: I’m all for couples recording their engagement, but the idea of us reenacting it for video content made Tyler and I squirm. We politely declined, and eventually started making our way back to the hotel.

I'd describe the newly-engaged feeling as similar to booking a fabulous acting job. Dancing around, jumping, smiling, telling random people the good news - yeah, it’s a lot like that. 

Needless to say, I was that girl - crossing Chicago intersections holding up my hand shouting “I’m engaged” in front of people who I’m sure could care less. 

Do you ever hear about those couples who get engaged and get free champagne or something? Yeah, we didn’t get that. Once we got to our hotel room we officially put the word out to more of our family and friends, eventually watching the ball drop on CNN as we rang in 2022. 

Need to say it was my most memorable trip to Chicago ever.

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Looking for your next great date night in Los Angeles? My boyfriend and I recently celebrated our 1-year dating anniversary. To mark the occasion, we decided to get dressed up and go a trendy bar  in Hollywood. We choose the historic Roosevelt Hotel. 

What is the Hotel Roosevelt famous for?
The Roosevelt is located on Hollywood Blvd., kiddie corner from the famous Grauman’s Chinese Theater – or well, TCL Chinese Theater now.  The hotel was established in 1927, and some of the silver screen’s most iconic performers have stayed there, including Marilyn Monroe, Charlie Chaplin, and Clark Gable.  In addition to a hip Tropicana pool area, the hotel also features multiple swanky bar spaces inside. 

Speaking of inside…

When you walk into the Roosevelt from the Hollywood Blvd. entrance, you are immediately thrust into a stunning Spanish Colonial décor. It’s honestly one of the prettiest places I’ve ever seen. 

Can you visit the Roosevelt Hotel?
​Even though it’s a working hotel, the cool thing is that you don’t need to be staying there to enjoy the space. You have your choice of multiple bars to enjoy a fun night out in downtown Hollywood. 

We decided on the Spare Room – mostly because it was the first bar we found, but we were still happy with our choice. This bar offers an upscale atmosphere without the loud crowds, so it’s perfect for a romantic and cozy night out with your significant other. Interestingly enough, the street-facing side of the bar features a one-lane bowling alley, hence the name ‘Spare Room’. 

The bar also features plenty of booths so you can sit and relax while you sip on your drink. 

Speaking of drinks…

Because of the location, the drinks will be higher in price. However, the great thing about the location is that you can start here, you each have a drink, and then walk to another bar in Hollywood if you want to stay out but save a little on the next round. 

Once you are done with drinks, I highly suggest taking some photos in the gorgeous Hotel Roosevelt lobby as well before you head out.

I recently traveled to Miami, Florida and discovered some very helpful info along the way. Here are some of my top Miami travel tips that first-time visitors should know. 
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Is Miami safe to visit?
Generally speaking, Miami is safe for travelers. However, there are certain areas that tourists should avoid such as the outskirts of Little Havana and the Wynwood Arts District. The main areas of these places are fine, but I would not suggest venturing too far away from the busier parts.
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As far as Miami Beach, we felt safe. That being said, you should still exercise caution, especially if you plan to party in the area. Avoid leaving your drink unattended or taking drugs from strangers, don't walk alone late at night, etc. 

Where to Stay
Miami and Miami Beach are two separate areas, though still close. Miami Beach is a stretch of island off of mainland Miami. While Miami is more of a city vibe, Miami Beach has the beachy, tourist appeal. Even though there are some great parts of Miami to check out, such as Little Havana and the Bayside Market, I would recommend booking your hotel in Miami Beach. This is also where South Beach is located.

The famous street in South Beach is Ocean Drive, which is where much of the action is. There are also plenty of hotels in this area too. Unless you are a 21-year old who loves to party, though, I advise staying further up Miami Beach to avoid late night noise. Our hotel was at 30th and Collins, and it was super easy to get down to Ocean Drive. 

Tipping 
One thing to know about Miami is that the tips are included in the bill. 

Transportation
One of the great things about staying near South Beach Miami is access to free trolley rides. They operate 7 days a week, have different routes, and run from 8:00 a.m. to 11:00 p.m. Of course, you can use ride shares or your own car to get around too.

Where to Eat
If you’re heading to Miami, you should definitely get some Cuban cuisine. There are plenty of great spots in Little Havana. I enjoyed Sala’s, especially since they also had live Latin music while we dined. Another great place to eat is Havana 1957 in South Beach. They’ve got an incredible menu and even include a piece of sugar cane with your mojito if you order one. Nice  touch.

Weather
Florida weather can be unpredictable, especially if you don’t go during the busy season, A.K.A. Spring Break. We knew we were taking a chance by going in September. However, don’t let the weather deter you if you can’t go during the Spring. We were there for 4 days and 3 of them were perfectly sunny. Our last day was the only time it rained, but it was just during the morning so it wasn’t bad at all.  

How long should I stay?
If you’re short on vacation time, you can definitely experience Miami in four days. The city is perfect for a long-weekend trip.