I Need To Stop Breaking Up with My Boyfriend

“Just do it,” I looked at myself in the mirror.

I keep breaking up with my boyfriend. But I need to stop. I know I cared about him. I cleaned his apartment the second time I came over. I can’t go to the grocery store without wanting to pick out something for him. I can’t go a few hours without saying his name sometimes. If his name was a curse word, I’d be a sailor. I want him there when I go out and when I fall asleep. I care about my boyfriend.

I broke up with my boyfriend – or the guy I wanted to be my boyfriend – two months ago. And that lasted two days. I told you, I keep breaking up with him. He probably has stopped believing me when I say it’s over.

That’s why I’m standing in front of the mirror.

Is it normal to break up multiple times?

I was reading a Cosmo article and “an estimated 44 percent of people ages 17 to 24 have reconciled and started over with an ex, according to a recent study by Bowling Green State University and the University of Wisconsin at Milwaukee.”

And I can testify that this vicious cycly is real. This was me at 24 when I started breaking up with my boyfriends and getting back together. Every guy I’ve tried breaking up with I came back to even if it was the next week and I told him he could come over if he didn’t kiss me. And guess what, it took about 30 seconds of him standing in my doorway for that post-breakup kiss.

But I needed to focus!

How To Break Up With Your Boyfriend:

I sent my boyfriend the breakup text.

“I cannot be your backup plan anymore…I cannot be with someone who doesn’t want to be with me or kiss me.”

I sent him this breakup text on Saturday night around 8 pm. The Cubs game was on. It was pouring rain.

Two hours later. No response.

Five hours later. Nothing.

The next morning. No word.

12 something – “Let’s air things out. I’ll call you later.”

I’m probably the worst person at breaking up with someone. I know what I want – a real relationship. But, men do this thing where they hook you without a commitment and they make you so happy and kiss you every so often and check-in on you enough that you become like a dog returning to its vomit. You can’t help but keep getting back together after his “hey. how are you?” texts and paying for his cheap beer – or even worse, stocking your pantry with his Tequila and Squirt and your freezer with frozen pizza for when you two get drunk together which is often enough.

If this were a terrible situation, you would get out. But, it’s not. And that’s why you can’t bring yourself to break-up with him.

You’re staring at your better half – you in the mirror – and convincing yourself that this guy, this man you’ve been dating all summer – is just not your boyfriend and most importantly, he doesn’t plan to become your boyfriend.

He tells you things like “I just got out of a relationship.” “You need to have patience.” or the best “I like how things are going and I see a future, but I can’t be your boyfriend right now.”

“Sweetie, when it starts to stink, you’ve got to take the trash out,” you look into the mirror and apply Dior lipstick.

“He doesn’t want to be your boyfriend.”

You’re standing there and then flip through Netflix and start re-watching Gilmore Girls – the one where Dean and Rory are being cute and get their first kiss in the market. Dean moved to Stars Hollow from Chicago, so this 20th time of watching Gilmore Girls re-reruns, you pick up on that and start falling for him like Rory did. You’ve seen where this relationship goes, but you can’t help but want it to keep progressing.

He – the boy you texted two days ago – finally calls. And, you finally have the small talk and then the talk. 

I don’t want to do this. I’ve tried all those games – not texting him back for 3 days. Going on dates with other people. Not inviting him to every event. And none of it worked.

I know that when I do this – when I sent the breakup text – when we had the talk – that I had to stop the games and stop wanting him to come back. I needed to stop this because being in this pseudo-relationship – the one where there’s no commitment. Where we can date other people. Where weekends are for our friends and family and you can have Tuesday night after 9 pm. I needed to be out of this limbo. This nothing that has turned into something to paraphrase You’ve Got Mail.

Again, I don’t want to break up with my boyfriend. I want to run into his arms and hug him and kiss him. But his kisses have become more reserved. He stopped adding “doll” or “babe” or “boo thang” to the text. I’ve become “hey.”

You think back to that fourth date. When he couldn’t go five minutes without wanting to kiss you.

You draw your face to your iPhone – we’re breaking up now. And you want to take in this last conversation. And this time, I mean the last conversation.

“I’d like us to still be friends,” he says. “I like hanging out with you.”

This hurts even more. I want that too – but I want to hang out with you and kiss you. I don’t want you flirting with other girls in front of me.

We say nice things like “you’re a great man, and handsome, and you have a good heart and a lot going for you.” He returns the gesture and says “you’re a good woman.”

And I say “okay.”

And just like that, it’s over. I block his number.

And then I do something dumb. I buy Halloween candy and buy a subscription to Match.com. I don’t know which one is worse – the candy or paying to find someone who wants to be my boyfriend.

After about four years of swiping and dating guys who were great but didn’t want to be my boyfriend, I’m taking things more seriously and upgrading to the world where people send you complete sentences and ask you questions like “what’s your favorite wine?”

You fall asleep numb.

The Day After You Breakup With Your Boyfriend:

I sit here. The very next day. And all I want to do is stay in bed and drink ginger tea and listen to r&b – that old school Usher. I put some foundation on. I straighten my hair and re-apply the Dior lipstick. I’m on my third outfit and the dishwasher is on. I finally ate something besides a mini Twix bar and it’s time to face the world. It’s time to stop thinking about this guy. This guy who I shared so much of my life with. Who was there for me when I finished the Chicago marathon – with flowers, a card, and an energy bar.

Who ran after me when we had our first kiss and I said, “I don’t want to kiss anymore frogs.” Who was my plus one to dinner parties and beer release parties. Who worked across the street from me downtown. Who made me feel giddy because he was so handsome and he had a good heart.

To say we didn’t have something was a lie. But according to How I Met Your Mother, you need two things to make a relationship work – chemistry and timing. And we only had one.

How To Leave Your Boyfriend and Not Text Him Back

So, what do I do now? How do you keep living life after you break up with the guy who has become more vital than your afternoon cup of coffee?

I text my closest friends and tell them I’m going to be texting them more.

I channel my energy into productivity. 

I already rearranged my apartment – you know for new energy.

I started drinking more – water that is.

And I go for walks. I enjoy the fall weather instead of sitting in bed.

This is day three. And I’ve re-read all of our texts. Gone through all of our pictures and remind myself that it was real. It was really great. And I’m one step closer to being with a guy who wants to be my boyfriend – because I didn’t just stay friends and leave myself emotionally and physically available to him.

I scroll through his texts again “You’re being cute today,” he would say. Day three is a bitch.

I check my phone every 5 minutes because I unblocked his number. I know, I’ll add self-control to the list.


Being Single Costs an Extra $2K a Year and Other Reasons You’re Poor

You took fake it till you make it too far.

We’re entering the summer months – which in Chicago is a very big deal. It’s that time where buying rounds of drinks (at every rooftop in the city) is important. We’re getting fake tans and taking yoga classes and getting the matching yoga pants that are trending on Instagram.

But before you start doing it for the gram (yes, we saw you throw out the Starbucks Unicorn Frappuccino), you might want to take some advice from the goddesses of being the plus one of the rich and the famous, Guest of a Guest. 

Guest of a Guest recently published a post detailing why you’re poor. They covered it all from Ubering every day (yes, it’s still cool to walk a few blocks, even in heels) to buying a name brand white t-shirt instead of the value pack at Target.

I did a double take when I saw that dating around can set you back an upwards of $2,000 a year. Ang then Guest of a Guest emphasized, “No, seriously, studies have demonstrated this.”

If you’re trying to save for a summer vacation and wondering why you have no funds to go somewhere and get an actual tan (Cabo, Meekanus, anyone?) then you need to stop what you’re doing and check yourself.

On the list (there are 13 reasons) included:

  • Buying name brand instead of bulk
  • Ubering everyday
  • Doing it for the gram
  • You’re single

For more financial advice, learn from this guru who talks about giving up Uber and brunch to save for bigger investments. 

Cheers for taking a moment to be financially savvy! No one will know that your white button down isn’t Burberry and if you’re staying at home drinking Barefoot wine and Netflix and Chilling instead of buying dinner for your next one night stand. We get it, you’re bad and boujee.




In a Saturated Market, The Only Way to Stand Out is a Resume

In what is being called an “unreal effort” on social media, one man’s attempt to date has gone viral. Joseph A. Adams put together a dating resume to respond to someone’s Facebook post asking for suitors.

Of course, Joseph is from Michigan, and he even created charts to showcase his interests. In case you’re wondering, Netflix and making bomb playlists are part of that chart – still unknown if they include Drake’s “More Life” or old school alternative from The Goo Goo Dolls.

According to Elite Daily, he didn’t get a date with the first Facebook post, but because he was prepared when this girl asked, other girls have noticed – and shared his resume. And it looks like he will have plenty of dates.

Although people look at the workforce as a saturated and competitive space, I don’t think anyone anticipated the amount of people they are competing with in the dating world.

There’s an estimated 50 million users on Tinder alone. Fifty million. And at 35 minutes a day, 10 million active users daily, it’s easy  to get a match but not be asked out especially when you move to other apps like Bumble, with time and gender constraints  – women have to say something more creative than “hi” to get a man’s attention.

I must say, he seems witty, he indicates that he’s educated and has a stable job, and he is relatable, but at the same time his extra effort shows that he’s serious. I mean damn, Joseph. It’s great. There are a few things that every girl wants to know before matching with someone from an app or the internet. And he didn’t cover all of them.

I agree that sometimes it’s hard to standout on dating apps and websites. All you really want to know is:

  • Are you available in the next few hours or days (please don’t be boarding a flight to London and match with me)?
  • Are you a reasonable height?
  • Do you have a job – and a career in mind i.e. something that says I’m looking at my life from another perspective than the present?
  • What are your intentions?  – are you going to knock on my door at 3 am to make out with me?
  • And, especially in the Trump era – are you a Republican or Democrat?

Of course, chemistry and conversations, scent, and availability are only things you can find out once in person.

After using dating apps since 2014, I admit that it’s painful that I’ve already re-matched with past suitors and I don’t know if it’s because they forget that we went out once or they thought we were friends and could catch up. You start to think that maybe you should go to events or join a sports league instead of swiping for Mr. Right (Now).

See Joseph’s complete dating resume below. Now all I want to know is if you saw this resume, would you text him or send him a LinkedIn invite?


Fat Tuesday and Mardi Gras Parties in Chicago

It’s that time of year when Gabrielle Union and Chicago Bulls, Dwyane Wade and everyone else wants to experience NOLA. But, Chicago is so nice right now. Like global warming brought summertime Chi to February nice. So, it might be time to indulge in Fat Tuesday, Mardi Gras festivities in Chicago.

We’ve got you covered for the Mardi Gras bar crawls and specials. Now all that’s left is finding some beads and figuring out what to give up for lent.

2017 Mardi Gras Bar Crawl Chicago:

Saturday, February 25th, it’s time to crawl to a few Chicago bars including Burger Bar and Sono Wood Fired Grill. For the cost of two cosmos, the tickets ($20) include bar hopping with a Mardi Gras mask and beads and enjoy food and drink specials along the ways.
The Mardi Gras Bar Crawl includes:
  • (2) $5 Gift Cards (Food or Drink)
  • Drink Specials ($3, $4 & $5 Specials)
  • Limited Masks & Beads Will Be Provided!
  • No Cover (You may still have to wait in line)
  • Photo Hunt & Online Contest for Best Mask!
  • Registration 2-4pm (Please do not be late!)
  • Portion of proceeds benefit local charity

Plus, if you are using Lyft for the first time, you can earn $50 in free rides.


Sign-up now for the Mardi Gras Bar Crawl on February 25th!

2017 Mardi Gras Party Bus:

Sometimes, you can’t even crawl, you need a bus to escort you between bars. And, we’ve also got you covered. This event is sponsored by MeetPeopleChicago, which puts on intimate and lively events in the city including this easy dating at one of the most romantic restaurants in the city, The Bedford.

Tickets include the bus that will take you to four bars in four different neighborhoods including:

  • Clark Street Ale House/River North
  • Rocky’s/Bridgeport
  • The Owl/Logan Square
  • Original Mothers/Gold Coast

Sign-up now for the Mardi Gras Party Bus on February 25th.

Mardi Gras Booze Cruise:

Tickets ($30-$40) include a Live DJ, Dancing, and A Drink At The After-Party! Catch breathtaking views of the skyline while aboard the booze cruise.

Sign-up for the Mardi Gras Booze Cruise on February 25th!

Sunday Sinners Mardi Gras Brunch:

Learn to make a classic New Orleans brunch including crab cakes with remoulade, grillades and grits and lemon bread pudding with dried cherries & cafe brulot.

Tickets ($80) include:

  • Crab Cakes with Remoulade
  • Grillades & Grits
  • Lemon Bread Pudding with Dried Cherries & Café Brulot

Sign-up for the Mardi Gras Brunch on February 25th!

Mardi Gras Madness:

If you want to start the weekend off with a little madness, go to Merchandise Mart on Friday, February 24th. My fellow Chicago blogger, Chi At A Glance has all the details including the oysters and French 75s for you to sign-up. 

If you would like to skip the night of debauchery for one fancy Mardi Gras cocktail or let’s face it, a lot of good seafood, Chicago has you covered as well. Carnival in the West Loop is having a Carnivale celebration on Fat Tuesday with Mardi Gras inspired drinks.

And just a personal tip, before a weekend of partying, plan ahead to indulge on the actual Fat Tuesday, Tuesday, February 28th off with Paczki Day and read about where to get them.

Let me know about your favorite place in Chicago is to get your NOLA vibes.






What Do City Girls Do During The Weekend?

January and Chicago winters in general is a time that you either get sick, get asked to cuddle, or Netflix and Chill by yourself.

One of my favorite newsletters, The Hustle, asked their readers to submit a selfie with what they did over the weekend. The results were pretty mixed and inspiring from a weekend of calling relatives and Netflix and Chill to a day on a plane.

Every weekend it seems like there are the standard options – go on a Tinder date, go to the bar, Netflix or read, and apparently meal prep and grocery shop are also popular as well as go to the gym.

But reflecting over this weekend, I didn’t really do any of those things. You can always check real time updates on my Snapchat (Rationalization) or my Instagram (@WindyCityCosmo), but for a whole snapshot of a city girl’s weekend plans during the winter in Chicago, here you go.

Cheers to saying no to cabin fever.

This weekend started off. I have been trying to take a break from dating -something I seem to do every year in January or February. As I started swiping, my friend invited me over. I got together with a few friends who were studying for their project management certification. We made pasta and garlic bread and talked about politics especially NATO and Donald Trump. Then we moved onto discussing whether I wear too much black, if we should make YouTube channels and the struggles in interracial relationships.

I took an Uber home and crashed on my friend’s couch. The next morning my friend had a day date – a breakfast date. She came back, and she helped me move some stuff into my new apartment.

She decided that some things have to go and we threw out dragged a dresser to the curb.

We went shopping for a few apartment things on State Street and then ate dinner at Nando’s on Wabash. Their chicken is everything.


She went home to Netflix because A Series of Unfortunate Events was released on Friday the 13th and then, she got ready for a party. I went to my apartment. I found the grocery store nearby and talked to my parents while I shopped for gluten-free waffles. That wasn’t the intent, but I always like to try something new when I shop. P.S. the grocery store is a ghost town on Saturday night.

My friend came over to my new apartment. And though we talked about going to a bar we ended up drinking cider, talking about relationships and watching the last episode in Gilmore Girls Revival (and surprisingly liking it more the second time watching it). My friend went to the Green Mill, and I fell asleep around 1:30 am.

The next morning I woke up and hit snooze. I rushed to take a shower and realized I forgot to buy soap. So, I used hand soap! Then I took an Uber to church. I met with my friend and we made plans to watch The Bachelor, though Nick is being a bit weird.

I took the Clark bus downtown and figured out how to get quarters to do this week’s worth of laundry (which by the way is at the bank, or if it’s Sunday, at Mariano’s). I had book club that afternoon so I was religiously listening to the audiobook “Born a Crime”. Pro tip: if you speed up the reading time to 1.5 speed, you can still understand the book and finish it. Yes, Trevor Noah’s book is amazing.

Book Club:

The painters came to my apartment early, so I took a longer walk through my neighborhood and went to book club. We drank mimosas and bottled margaritas and discussed our feelings about Trevor’s life i.e. is he funnier that John Stewart, does South Africa have the most corrupt cops (they don’t, it’s actually Haiti – yes we looked it up) and how serious is domestic violence (in Chicago, see here), what does it mean to hustle, and what we learned about Apartheid.

Football and Politics:

In between this discussion, the Cowboys vs. Packers game was on and we watched the incredible game. The last two field goals were everything.

We lingered and talked about Donald Trump’s inauguration and updates on starting a career. Everyone left and I started falling asleep to Princess Bride. I took an Uber home and finished drying my clothes.

So I guess my weekend was ordinary – shopping, chores, and hanging out with friends, but honestly, I live for great conversation, amazing company, and good books, so I’m pretty happy.

What did you do this weekend?