A Chicago Man and Woman’s Take on Dating Apps

A Chicago Man and Woman's Take on Dating Apps

Mallory Lepage and Rob Johnson share a Chicago man and woman’s take on dating apps.

Mallory Lepage – A Woman’s Take on Dating Apps

Dating digitally has made it somewhat ‘easier’ to ‘meet’ people. Now, we have the luxury of dating from the comfort of our living rooms without the perfect date outfit, makeup or liquid courage. Certainly, Tinder pave the way however now we have so many options to choose from like Hinge, Bumble and Happn. Now, the question then arises of which app to use and how to use it.

Swiping and matching: Quality vs. Quantity

Swiping left or right based purely on appearance is extremely shallow but is sadly the reality of the majority of these apps. Women by nature take longer analyze a potential suitor which in turn, yields less matches. Both sexes should take this into consideration when building their profile. Choose honest and recent photos that display different sides of your personality. Keep your description concise and interesting enough to be intriguing but write a description as it will give the person on the other side an opportunity to learn something small but exciting about you. Based on how serious you are about meeting someone try to be open. The ultimate goal is to meet people outside of your circle but also remember to be cautious for the match who just wants an immediate hookup.

The First Impression

Traditionally, the men courts the woman. I’m more traditional when it comes to dating so I typically allow the man to reach out first. Sure there are occasions that I reach out the man first but that usually backfires in my face so I’ve stuck to the same behavior as I do when I meet someone organically at a bar – let the man lead the way but once the conversation has started you’re equally responsible for keeping it alive and asking compelling questions. Try to find common interests and be yourself, it’s easy to agree on topics but stay true to who you are or the first date with be a total disaster.

Get Offline Quickly

The duration for which you talk before you meet is a delicate matter. Talking for too long before you meet is a slippery slope but meeting too soon can be legitimately dangerous especially for a woman. There are several contacts in my phone book that come out of the woodwork from time to time whom I’m never met but may have talked to in these apps. Similar to shoes and hand bags, I categorize these men for different needs in my life:

— The guy that introduces himself asks you how you are and immediately asks to get drinks. Stop. While I appreciate your flattery and assertiveness, I need to verify that you aren’t a serial killer or stalker.

– The guy who is in from out of town and wants to get drinks that night. This is a hookup. There’s no exception to this rule, just a hookup.

– The guy that never makes concrete plans but continues to talk to you. He’ll come back around when your college team wins a game or its your birthday. Maybe a late night text but you’ll never actually meet him, and maybe you’re okay with that but cut him loose.

– The guy that actually is a gentlemen. He takes you out for a few dates but then like an urban legend, vanishes.

Dealing with rejection (or not)

Both scenarios will absolutely happen. You will be shocked, at times, with the gorgeous suitor that matches you on the other side. Sometimes you need that confidence booster to remind yourself that you are indeed a catch. Reversely, you will be let down. Matches will be brutal, whether that means removing your matched profile, vicious comments (it happens) or simply no response you have to keep in mind that you are brave for trying this and putting yourself out there. There is a match for every soul and you’re just trying to find yours, these people don’t know how wonderful you truly are so you cannot take offense to rejection but rather try to do the opposite. Find encouragement from all the matches that find you beautiful, intriguing or fun.

Rob Johnson – A Man’s Take on Dating Apps

Dating is hard. On one hand you have put yourself out into the (online) world to meet someone, there are options, but so few quality matches. Dating apps like Hinge, happn, Tinder and the like have brought the dating culture to your phone. If you want to be successful using these dating tools you must change your mindset about dating and how you go about meeting someone.

Lets first look at how dating apps are different for women. It’s not uncommon for a woman to match with every guy she swipes right to and of those men, a majority will say something inappropriate or inadequate (“Whats up”). I have had conversations with women who share their frustration with the endless amount of subpar men sculking in the online dating pool.

Swiping and Matching

Matching is a numbers game, but you want quality matches. Look for traits that you find attractive. For instance, I’m not much of a sports fan so I would not select women whose photo is from Wrigleyville wearing a Blackhawks jersey.

It is okay to be broad in your search at this point because you are just trying to get matches. You should not invest much emotional energy at this point because you likely won’t match most of the women you see.

First Impressions

Once you have matched with a woman, the best way to stand out is to start the conversation by saying something sincere and engaging. I usually start with:

Hello _______, it’s nice to “meet” you.

You then can follow up with a thought provoking question like:

What excites you? or What are you passionate about?

I have found that by asking a question, you are more likely to elicit a response. This shows that you have an interest in getting to know them. You’re not just commenting on her looks or making some generic joke.

By showing a genuine sense of interest, you will put yourself far ahead of anyone else.
This is because, most men try to project themselves onto their match: I think you’re good looking, I’m funny, I just want to hook up.

I also like asking a question because you get a chance to learn something about her. I once asked three women the same question: “what are you passion about”. Here were their responses:
“lol, i don’t know. i cut hair” – Jaine (pseudonyms)

“I’m really passion about women’s rights and addressing issues within the black community. I work with a youth group now that helps young girls.” -Selena

“as seen on tv infomercials and exotic bird watching.” -Brittany

Each response is telling. It is evident that Selena is a passionate and motivated women. Brittany probably is sarcastic AF and Jaine probably isn’t worth my time.

Get Offline Quickly

I try to spend as little time as possible messaging within a dating app. You are trying to meet someone, not have a pen pal. The longer you stay on an app, the more likely one of you will stop talking or loss interest. Usually, you can tell within the first three messages if there is a high enough level of interest to continue the conversation and meet.
Ask her out on a date or for her cell phone number. If you ask her out on a date, and she says yes, set an exact time and place. Setting an exact time and place for the date shows that you are committed to get to know her and want to continue to get to know her.

You will not really get to know a woman until you meet and can continue to develop your relationship without the use of dating apps.

Dealing with Rejection

It is easy to get burned out. There will be times where someone will just drop off the face of the earth for no reason. This is a symptom of our dating culture. Men and women are faced with so many internal and external distractions that often dating or talking to a stranger is not appealing.
It should not be taken personally.


Dating does not have to be as hard as we make it. If you take one thing away from this article it should be that your dating life should not live online. Using dating apps as a tool to find potential matches, but once you have found a women who you like and is interested in you, meet in person, share each other’s company and ultimately have fun.


It’s interesting to see what’s different and the same between men and women. What have your experiences been with online dating in Chicago? Sound off in the comments!

Categorized as Dating, Life

By Mallory Lepage

After living in several of the greatest cities in the country, I made Chicago home a short three years ago. Chicago is the perfect hybrid of the Midwest relaxed mentality and chaotic city life that allows me to enjoy so much it has to offer. I’m equal parts tom boy and glam girl, I love watching sports (Go Green!) just as much as I enjoy taking hours to get ready for a night out on the town with my girlfriends.

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