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Then & Now: 20 Years of Dating, Sites, Apps and Rules

Like with many different things in our lifetime, a span of 20 years is bound to bring some significant changes. And at no time does that feel truer than now, in this digital day and age when change feels so constant that it can be difficult to stick with at times.

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For better and for worse, dating is one of those integral aspects of our lives that’s constantly touched by change, especially as the online side of things has made its way to the forefront over the last 15 years or so. But as things have changed, AskMen has been right here, helping you make it through every step of the way.

That’s why, as the site celebrates turning 20 years old this month, we wanted to take a look at just how far things have come since the late 1990s. The following is a snapshot of where we’ve been, as well as where we are now.

Meeting Someone, Then & Now

Then — You’ve got two solid options: get out there and be social, or have your friends set you up with someone they know. If you go the blind date route, you’re literally going in blind; there’s no way for you to check this person out beforehand, unless your buddy physically gives you a photo of them. Good luck!
Now — Tinder, Bumble, Grindr, Facebook, Instagram, eHarmony, Match ... the list goes on. Go ahead and slide into those DMs before someone beats you to it.

Then — Find out what you can from friends and friends of friends. Realize all of the information was wrong when you meet face-to-face.
Now — You are a social media sleuth. Check their Facebook (they do have one, right?), their Twitter, their Insta, their Pinterest or maybe even their LinkedIn. Just don’t accidentally like a photo from two years ago, or you’ll look like a major creep.

Getting in Touch With Potential Bae, Then & Now

Then — Sure, cell phones are around, but who even has one of those? You’re going to be calling a landline — you know, one of those stationary telephones with a spiral cord that loves to get tangled. Everyone except for the person you’re trying to reach will answer. You’ll have to leave a message with someone, but unfortunately, there’s no real guarantee that it will ever reach the ears it was meant to grace.
Now — You’re not a caveman ... just text them. Use some emojis while you’re at it.

Then — Maybe you’ve added them to your contacts on AIM or MSN Messenger. Maybe you’ll get lucky and catch ‘em signed on to their dial-up, or maybe their little icon will tell you they’re away with a cheesy lyric-filled message. Either way, tread carefully: there’s always the possibility you’re getting trolled by their little brother.
Now — Get the Snapchat streak going because that’s how you know it’s real. Really, though, it’s easy: you hardly even have to have a conversation anymore. Just take an artsy selfie, scribble out most of your face, insert a self-deprecating yet playful message about how ugly you are, and send that baby on its merry way.

Becoming Your Best “Romantic” Self, Then & Now

Then — Stand in line at the local grocery store or pharmacy and pretend you aren’t looking at the glossy covers of women’s magazines that promise to teach you about “the hottest sex tricks you have to try.” Sneak a glance at some of the articles, mentally take a relationship quiz and then internally freak out after finding out you’ve been doing it all wrong.
Now — The articles have migrated online and multiplied a thousand fold, if not more. Travel to the darkest corners of the Internet. Find out anything and everything … just make sure you’re not looking at it on your work computer. They can track that.

Spending Time Together, Then & Now

Then — Plan cute dates frequently, whether that’s going out for ice cream, seeing a movie, or playing mini-golf. Hang out at the mall, because at this point, that’s still a thing. Picnics in the park are popular too, as is rollerblading or taking a long, leisurely hike (but actually).
Now — Does binge watching “Stranger Things” with your blackout curtains permanently closed count as a cute date?

Then — Stay up until an ungodly hour talking on the phone about life, your hopes and dreams, what you had for dinner, what you’re doing next weekend, regrets, your fears and your most embarrassing moments — any and all topics under the sun. Wake up the next morning, receiver still in hand, busy signal steadily thrumming in your ear.
Now — Fall asleep without responding to their goodnight text. Wake up the following morning to a scathing diatribe about your qualities, not only as a partner, but also as a human being. Alternatively, get hit with radio silence for the first half of the day. That’s dating for ya in 2019.

Then — Write each other cute messages on sticky notes, leaving them in places where they’re likely to be found. Author full-on love letters sharing or reinforcing your true feelings. Cobble together the perfect playlist filled with the likes of Savage Garden and Backstreet Boys, burn the songs onto a CD, create your own cover art and relish the look on their face when you give it to them.
Now — Text each other using incomplete sentences sprinkled with copious amounts of hearts winking kissy faces and eggplant emojis. How else would you get the message across. And by the way, what in the hell is a CD? Share a YouTube link to Lizzo’s latest banger.

Calling It Quits, Then & Now

Then — Man up and break it off in person, or stop answering the phone. Your call.
Now — Man up and break it off in person, or stop answering the phone. On top of that, you can now block their number, unfriend them on Facebook, unfollow them on Instagram, unmatch on Tinder, ignore their Snaps, or sign up to fly to Mars with Elon Musk.

In 2019, your choices are endless.

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Logan Hansen, Khareem Sudlow