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A Chicago Man and Woman's Take on Dating Apps
Dating, Life,

A Chicago Man and Woman’s Take on Dating Apps

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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!
Dating, Life,

How to Make Love Last

Through thick and thin.

I always thought this was a great analogy to describe the type of love you feel towards a partner or spouse and what you are willing to do for that person. Love is wholeheartedly giving yourself to someone with the hope that they will do the same.

If you think about why relationships do not work out, they ultimately boil down to four principles: trust, respect, loyalty and freedom. At the core of any happy relationship, these principles are the cornerstones.

Trust is by no means easy to build, but fundamental to the security and health of any relationship. Think about how many times you have worried about: who your significant other was hangout out with, what he or she was doing or if they were honest about where they were. These sort of thoughts can erode your spirits and question your feelings towards the relationship.

It is not easy to trust someone and should not be given blindly. When your partner has shown that they respect you and can be loyal, you can give trust in return, the love will build on itself.

I’ve found that the best way to avoid misunderstandings in a relationship is to be respectful towards your partner’s thoughts, feelings and needs. (To clarify, by misunderstandings, I mean fights, resentment and anger towards your partner). If you can make an effort to understand why your partner feels hurt, you will grow closer together.

Communication is key, be open about how you feel and willing to listen.

Loyalty is about us, not you or me. Hold your partner in as high of light (or higher) as yourself. A strong couple is like a team; they work together and are considerate of the other person’s feeling. Understand that your actions affect everyone in the group.

Love is about letting the other person be free. While you are loyal to one another, you are also individuals with your personal needs and goals. Be respectful of the time your partner may need to themselves and be comfortable with your own time. When you can build loyalty and trust, it is easier to enjoy each other when you are together or apart.

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Dating, Life,

Who Should Pay the Tab on the First Date?

A hotly contested subject with’s writers is: Who should pay the tab on the first date? The girl? The guy? And why? Take a look at both sides:

Rob Johnson, representing a Male’s Opinion:

The simple answer- its depends.

On what? It depends on how familiar you are with the person you are meeting. If you just met someone at the bar, going on a first date or in a relationship, there should be a different expectation to buy someone drinks, dinner or pay for a  night out.

If you are going out with the hopes of meeting someone, that is to date or hookup, I would not buy or accept drinks. Until you know that there is a genuine level of attraction between you and the other person, don’t invest too much of your money or energy.

Too many women use their looks or fake sense of interest in a man to their favor. This mindset to dating tarnishes the allure and spark of potentially meeting someone. Just like the man who assumes you own them something because he bought you drinks.

When you first begin going on dates with someone, it’s a good idea for the guy to pay. Its a simple act of flatly, that is not only respectful but shows that you have a vested interest in getting to know your date and build a sense of attraction.

Once you are going on dates regularly, it is fair to rotate who pays. I typically follow the rule of thumb, whoever initiated the outing, should pay.

Source: Wikipedia

Source: Wikipedia

Mallory LePage, representing a Woman’s Opinion:

Should men take the lead and pay for the first date to maintain a slight bit of traditional dating to allow women to practice being courted?  Here lies the debate of who picks up the tab for the first date. In a poll conducted in 2013 by LearnVest and T.D. Ameritrade, 55% of men said they thought the man should take the check while 63% of women expect the man to pay.  There is noticeable gap of inconsistency here.

From time to time, I find myself having similar conversations with both men and women.  Men often complain that they have to spend an enormous amount of money on numerous first dates whether it is dinner, drinks or both.  In these conversations with male friends and relatives I’ve found that they haven’t really put much thought into what women invest in for a first date.  In the defense of women, my dispute is the amount of money and time that we spend annually on products and services to maintain the way that we look in attempt to charm an attractive suitor.  Recently, I sat down to calculate the approximate amount of money I spend annually on hair upkeep (cut and color), hair products, hair appliances, makeup, face products, nails and that monthly visitor.

The results were staggering.  Annually, I spend roughly $5,000 on the bare minimum. This does not include products or services that men may also utilize including facials, massages, manicures/pedicures, clothing, jewelry, shoes, birth control, fragrance, gym memberships, body lotions, undergarments or lingerie.  I would consider myself to be in the median of this number.  There are women that spend much more than I do especially if you’re factoring in any form of Botox but also women that spend much less time and money.

A man paying on the first is not meant to undermine the strides we’ve taken for feminism and gender equality. As long as women are giving birth, there should always be some variation of obligatory practices that men should abide by including opening doors, allowing women on and off elevators first, arranging the evening, walking on the traffic side of the street and paying the bill on the first date.  Keep in mind; this is just the first date, beyond the first date or even first round of drinks it’s more than appropriate and acceptable for the woman to step in.

So who should pay the tab on the first date? Share your opinion in the comments!

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Dating, Life,

Top Ten: Cheap Chicago Tinder Dates

Many of my friends have been in situations where they’re planning a first Tinder date but are unsure of what to do. Keeping in mind that they might end up not even liking the person, it’s important to find cost-effective solutions to get to know someone.

Cheap Chicago Tinder Dates

  1. Go to the beach.

    Cheap Chicago Tinder Date - Beach


    While going to the beach is limited to the (few) summer months in Chicago, this is actually a nice, low-key way to get to know someone new. You can BYOB (at your own risk!) instead of paying an expensive bar tab. You may also get to see what your date looks like in a swimsuit. Win-win all around. For those who like to multi-task, the beach is a great opportunity to soak in the sun and play a game of beach volleyball, so that even if your date sucks, you can cross gym and tan off your list for the day (the only thing left to do is laundry!).

  2. Go on a picnic.

    Cheap Chicago Tinder Date - beach


    Ok, it might sound lame to you, but there are so many beautiful parks in Chicago. There’s the Chicago Botanical Garden, Millenium Park, and more. You can even visit the Lincoln Park Zoo to make it look like you really planned things out. If you’re a foodie, make some delicious sandwiches to really impress your date. Have them bring the booze. Sharing is caring (and cost-effective).

  3. Go on a bike ride.
    Cheap Chicago Tinder Date - Bike


    Most Chicagoans already have a bike, but Divvy day passes are only $7 and are a good excuse to explore Chicago while getting a cardio workout. I highly recommend riding the lakefront path for a picturesque view of Lake Michigan. You can even tie in the picnic or beach idea if things are going well and you want to extend the date.

  4. Improv shows.

    Cheap Chicago Tinder Date - Improv


    There certainly is no shortage of improv shows in Chicago. They make for a great first date because they help break the ice. Tickets range from free to $20 per person, but everyone has an improv friend looking for audience members (just ask!). I suggest getting your buzz on before going in (ideas for happy hour coming up!), and buying something to sip on once you get to the theater. Here are a couple solid options for improv shows:
    Second City
    iO Theater

  5. Go to the Movies.
    No, I’m not talking about the typical expensive movie theater route. See a post I wrote awhile back about cheap movie-seeing alternatives.
  6. Check out a concert.

    Cheap Chicago Tinder Date: Concerts


    Depending on how discerning your tastes, Chicago has plenty of shows in the $10-20 range any night of the week. Another option worth looking into is Jukely, which offers “unlimited” concerts for $25/month. To guarantee a plus-one, you can pay $45/month for “unlimited” concerts for two. Jukely represents a lot of Chicago music venues, so there’s bound to be something you (and your date) will enjoy. Plus you’ll seem like a badass for having concert ticket hookups.

  7. Go out to eat (or drink).

    Cheap Chicago Tinder Date: Eat


    Let’s talk about a unique approach to the standard first date plan. Before planning a date, check out SmallTabs, which has aggregated happy hour specials from almost 500 bars in Chicago. You can organize your options by day of the week and Chicago neighborhood.

    Also worth mentioning are some cool bars that will give you an extra bang for your buck. Check out Guthrie’s to test your date’s hand at various board games. Headquarters, which has two locations (River North and Lakeview), pairs free arcade games with craft beers and specialty cocktails.

    Another option for saving a few bucks your meal is to sign up for Spring Rewards. Spring Rewards allows you to be a Cheap Ass on the sly.

  8. Batting Cages, Mini-Golf, etc.
    If the idea of getting your date hot and sweaty gets you going, consider doing something active. Sluggers tends to run Groupon deals all the time for their batting cages. And, although I haven’t personally been there, Diversey Range seems to have decent pricing for mini-golf ($10 per person).
  9. Art Gallery Openings.
    Cheap Chicago Tinder Date: Gallery


    A rather unique approach to a first date is attending an art gallery opening. This is a good way to open up and get into your date’s head. It also makes you seem cultured. Plus, there’s usually free wine.

  10. MuseumsArt galleries and museums? You must be a really classy date. Several of Chicago’s finest museums have free days once a week/month/etc. Check out Choose Chicago’s list that breaks down where and when to go.

So the next time you go on a first Tinder date, stand out from the crowd and do something interesting. Or at least save some money before you decide if your date is worth it.

What cheap Chicago Tinder dates have you gone on that you would recommend?