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The Evolution Of Modern Dating: Part 1

It seems shocking in retrospect that we as humans could actually keep relationships going before technology. But at the turn of the century, everything began to shift.

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Forty million Americans now roam online dating sites in search of their better half. In fact, 39 percent of couples report meeting online, compared to only 22 percent in 2009. It's surprising how much online dating has displaced the role of friends and family in meeting a life partner. And it shows how our relationship with technology is deepening to a whole new level. How did we get here and how does this new trend impact our lives and our society at large?

In order to answer these questions, I need to take you back to a place where smartphones don't yet exist: the 1990s. Considering I had just graduated from diapers during this time, I'm going to let someone else tell this story. Meet Dawn, a 51 year old entrepreneur from the American Midwest. Dawn’s dating journey spans three entirely different eras: letters, pagers, and call stations in the ‘90s, the highly stigmatized online dating days in the early 2000s, and the era of Tinder swipe parties in the 2010s. People say dating used to be more simple back in the day but after hearing Dawn's story, you'll think twice. But I'll let you decide for yourself…

Pre-cell phone dating (1990s)


Dawn: So I was dating in Oklahoma City in the early ‘90s, then I went to work for Royal Caribbean Cruise Lines and then I moved to the cruise ship and I was on a cruise ship for five years. We would be on board for six months, never leaving the cruise ship. So it was kind of funny on the cruise ship because most people had two lives. They had a life on the cruise ship and then they had their lives at home or wherever they went to. In my case, I would come home for for four months and kind of see the same person I had been seeing at home before I left for the cruise ship. Then I would also go travel and meet people along the way during that period of time, then go back to the cruise ship. It was a very odd lifestyle and a lot of that was because, what you didn't know about the future was that we didn't have cell phones! So that environment did not lead to being able to communicate very well.

Taylor: I was just wondering, how do you keep in touch with these people? I guess through email?

Dawn: Letters. There was not an email situation. In fact, I was on the cruise ship when they created a position to move computers on board. So normally we had computers on the ship, but we did not have the Internet, obviously (that process happened really after I got off of the cruise ship). Basically, we had an I.T. person that would be on the cruise ship and they would upload information that they got from a floppy disk.

At the end of the day, there was no communication via email for any of us with anybody that we were dating. It was all the letters or satellite phones on the cruise ship, which were extremely expensive, like twenty dollars per minute to talk. So you didn't do that. So then you would get off and go to what they called a call station and you would pay for so many minutes of phone time or the computer time and you could get on the computer that way.

Taylor: So, not so easy to communicate. And it sounds like you were on-the-go quite a bit too. Like you said, when you weren’t on the cruise ship, you were traveling a bunch. So what was your main form of communication with the guys that you met and wanted to keep in contact with?

Dawn: Letters. Letters that would take a long time to catch up because somebody would send me a letter to my Oklahoma City address at my mother's place, then it could be a long time before I received it. If I was on the cruise ship at the at the beginning of of a term of six months, then she would mail the letter on to me there. I would get off the cruise ship, call this call station, tell her which cruise ship I was on, tell her what address to send things to, and she would send me my mail. And then, you know, when I was off of the cruise ship, people would still just mail my mother things and it would take a minute for me to get them. I usually would just sit at my mom's house until I went back to a cruise ship.

Taylor: Right. OK, and then from these letters, how would you even try to arrange to meet up? It seems like it would just be so difficult.

Dawn: It was! It was really difficult. I mean, I can give you some examples. There was a bit when I dated somebody from one of the islands that I met on Grand Cayman Island. I dated a firefighter there.

And when I would stop off in Grand Cayman, he would come to the cruise ship and meet me. So in those kinds of ways, it was really easy. But I was also a 20-something year old kid. So, I mean, it was really difficult to meet up, but sometimes it was beneficial because when you're in your 20s as a female, sometimes you just don't want to deal with confrontation. So if I didn't want to talk to somebody anymore, I would actually ask to be transferred off of the cruise ship. Or I would in the example of this guy on Grand Cayman, I just wouldn't get off the ship to go talk to him. In that case, he would come and beg the officers to beg me to come off the cruise ship, you know?

It was really funny, too, because the way we talked was through pagers. So an officer would page me at the purser's desk and then he would tell me what number to call him on and it would be a cruise ship phone that was sitting near where he was. I would pick that like an extension like in a hotel. I would call that number and he'd say, “You have to come down here. He's here. He's got a present for you. I was like, “No, tell him I'm not coming!” And here we are trying to get guests on and off the cruise ship. So it was really funny to know all the behind the scenes.

Taylor: Even though it sounds incredibly difficult, it also sounds incredibly romantic. I mean, today's dating culture pales in comparison to back then when you were writing letters and planning to meet someone at the cruise dock that you haven't seen in months. I mean, now you to send out a message that takes about five seconds and you have a date by nightfall! So how would you describe that whole experience?

Dawn: I think definitely there was a build up to it. I don't know if we had less anxiety about it. I felt like we had anxiety, you know, because you were like, “Is he going to call me?” And there were days that you would just be looking every day in the mail for something, or you would be waiting to hear if there was a message from someone. So there were a lot of different levels that you were just waiting. But I don't remember being real anxious about it. And now if somebody doesn't get a text back within a minute, you know, everyone's second guessing the whole relationship.

Taylor: And did you have misconnections? Like maybe you left the day before he sent a letter?

Dawn: Oh my god. It was just the worst. The boyfriend that I had that was on again, off again. You have to realize I put him through hell for three and a half years to the point where he finally moved on. I remember when he moved on, I just was like, “Well, shit, he moved on. That's not fair. I was going to eventually marry this guy!” You know, I was running around having a good time thinking I was going to come back and marry him. So when he left me three and a half years later for someone else and wrote me a Dear John letter, I got that letter and I came running home and fought for him to win him back and was going to stay off of the cruise ships. And I remember he was really involved with this girl and he was trying to date both of us. I was okay with that because, of course, I left him so much. But I wanted him to choose between us after a month and a half and he didn't do it. He was like, “You've put me through hell for three and a half years.”

So when he didn’t choose, I remember I called him one time and left him a message and he didn't return my call within a day or something. So I called the cruise ship and said, “Hey, I'm coming back.” You know, I'm not waiting around on this guy to figure it out. So I scheduled that to happen and then he called me back and he's like, “Oh my god, now I want you back.” I was like, “Well, I've already said I would go back on the cruise ship!” So there was that whole missed opportunity for us because I went back to the cruise ship a while and I was literally driving to the airport to get on the plane when he called me to say, “Hey, I want us to work out.”

But I went back to the cruise ship. I got on the cruise dock because I was already in Miami and I got on a cruise dock and I called him from the from the payphone. We came up with a plan. He had a lot of credit card debt and I was able to pay all of my debt so I was debt free. So I said, “Well, why don't I go back on the cruise ship, and then that way we will pay off your credit card debt and in six months we'll get back together and we'll be able to get married and we won't have any debt?” So that was what we agreed to do when we got off the phone. Then I got off of the cruise ship in Jamaica to call him. And when I called him up on the payphone on the dock in Jamaica, the other girl answered his phone, at like six o'clock in the morning.

I remember I just hung the phone up and we didn’t talk for like a year and a half. His excuse for that a year and a half later was, she had just dropped by to pick him up to go somewhere six o'clock in the morning. So if we had cell phones, we'd have been calling each other and possibly able to work that out.

Taylor: Yeah, it would have been easier to have those more serious conversations. I guess he didn't know that you were planning on marrying him when you were done with the cruise ship, until it was too late.
Dawn's nomadic lifestyle, combined with the lack of technology, made her dating life complicated, to say the least. But even homebodies had a difficult time connecting with potential mates. Before cell phones existed, you had to call your potential partners landline. This was almost always shared with parents and siblings, and you never knew who was spying on your calls. Of course, it was purely a matter of luck whether the person you were anxiously contacting was even at home. Most times you'd get the landlines answering machine, which was like voicemail, but with cassette tapes. And a lot of the time messages were incoherent. But let's just assume you were lucky enough to connect via that telephone wired to your kitchen wall. Then what? Well, then you had to arrange to meet at an exact location at an exact time. And if your date was running late, you'd have to stay in that exact spot for a minute, maybe even hours. It seems shocking in retrospect that we as humans could actually keep relationships going before cell phones. So, yeah, dating wasn't as simple as people make it out to be. All of it just makes you wonder, what if, for example, what if Dawn and the guy she was planning to marry had cell phones? But all of that was about to change. In 1997, Dawn remembers getting her very first cell.

Cell phone dating (1990s)

Dawn: When I came out of my marriage, we all had cell phones and I remember having a cell phone. But texting was not a thing and definitely not pictures, but at least we had cell phones, so that was a step up. But I don't remember the cell phone being a huge deal even in ’97.

Taylor: Oh that’s surprising. I was just going to say that must have changed everything for you…

Dawn: I mean, I still waited for a phone call from whatever men were in my life. Like, it wasn’t a really big deal that you had your cell phone. You know, you still were waiting around for phone calls, and texting was definitely not something that you did or that I was really doing at twenty seven years old.

Taylor: I know you didn't really feel anxious to begin with, but I would just assume that there would be a lower level of anxiety just knowing that there wasn't going to be any sort of misconnection or miscommunication, because you had a cell phone on you.

Dawn: In my mind, it didn't feel any different than the cruise ship days, which is weird to me. Like in my mind, I didn't feel like, “Oh, this is easier dating.” It could have been because I was young and in my 20s and there were so many people and so much availability, you know, and all the things that were happening around me were just happening. So I didn't have much anxiety about it. I didn't have a lot of anxiety about dating until after my second marriage in the 2000s. The 2000s is when it got weird.
Dawn says she didn't have a lot of anxiety about dating until the 2000s when things got weird. So what exactly happened in the early 2000s? Well, let me set the scene for you. By the late ‘90s, early 2000s, online dating was exploding. In ’96, had 100,000 users, but only five percent of Americans had internet access. Then in ’98, hosted at 1.8 million profiles after they crafted a huge PR campaign to change the stigma that it wasn't only for the socially awkward. Then You've Got Mail made its premiere in ’98, transforming online dating stigma into every single woman hoping to find a Tom Hanks in their inbox. (Meg Ryan clip from You’ve Got Mail: “I turn on my computer, I go online, (welcome), and my breath catches in my chest until I hear three little words. You’ve got mail.”) So just imagine what it must have been like when Dawn, just coming out of a divorce in 2000, found herself amidst an entirely new digital dating world.

The dawn of online dating (2000s)

Taylor: Let’s flash forward to the year you came out of your second marriage in 2000. Was that a whole new world?

Dawn: That was that was an entire new world in the 2000s. I remember not really wanting to go and drink beer or work real hard to organically meet people, because I was busy working and raising children. So I remember being at work and then coming home and saying, “You know, it's 9:00 p.m. I live in a small town, I'm going to get on Craigslist.”

I remember, I put a Craigslist ad in. You know, I was bored. I just wanted to communicate with people, men in specific. I talked to probably hundreds. I want to say that very first weekend I met somebody that I dated on and off for four years. That’s when all the anxiety with the phone came up because texting was starting to really happen for me. So everybody reads into the texts. I remember trying to just do background checks. I remember one of the main things I did was add my girlfriends to my Find My Friends when I went to go meet him, because I wanted them to be able to know where I was at and what I was doing. So, you know, there's anxiety there. There was just a lot of things to consider. People telling you you're crazy for meeting someone off Craigslist.

Taylor: Right. I was just going to ask about how strong the stigma was. I know there was a lot of stigma around online dating and I'm assuming Craigslist was probably even worse.

Dawn: Oh, yeah. Everybody was like, I can't believe you’re doing that. Well, you know, me and this guy that I ended up dating on and off for four years; we were very compatible. It became a big deal right away just three months after my marriage, which was obviously too quick to get involved seriously. But I wasn't using Craigslist as a serious tool. You know, I was just trying to dip my toe and talk to people. People used to make fun of us all the time because we met on Craigslist.

Taylor: What was going through your mind the first time you were using Craigslist for online dating?

Dawn: I remember just thinking that it was fun, and thank god I don't have to go sit at a bar and drink beer to do this! Communicating with people and reading into their crazy responses or, you know, you kind of immediately knew who somebody was because he would send you an awful sexual innuendo type and you're just like delete, delete. You had a lot of power in it.

Taylor: Right. That makes sense. Whenever you said that there was anxiety around texting at the time, why was that? Was it just because communication could be misconstrued?

Dawn: I think it was because like, what do you write back, and how fast do you text back? It’s like, what are the rules here? Like from from school age communication and dating was all about talking in letters and will you be my date to the prom? And there was not all these different ways to communicate. Now all of a sudden there's Facebook. My ex husband, actually, had an affair and he met and communicated with his this woman through a fake Facebook account and the Facebook messenger. So there were all these new ways to get dating. And what were the rules in between that? You know, like my daughter who grew up with texting in this form of communication, it's a whole lot easier. You know, they were making up the rules, whereas when you're an older person and you're re-entering into this stage and you don't know the rules, you’re like, “Well, what are the rules?”
Dawn wasn't the only one trying to navigate this new world. Meet Rob, a 61 year old founder of a renewable energy company called Terrastar Energy. Rob was also just coming out of a divorce and found himself in a whole new dating environment. The year was 2005 in a small town in North Carolina.

Online dating (2005)


Taylor: Ok, so let's talk about 2005. You had just come out of your divorce. You were ready to start dating again. What did you do?

Rob: I heard about the online dating stuff and it just sounded really fishy to me. I didn't want to give up information, so I just didn't do it. Then things weren't working out with this girl and when we broke up, I thought, I'm going to give this a try. So then I tried I was actually fairly happy with I mean, I had to overcome a mental hurdle to do it because you're putting yourself out there. Now, I wouldn't think anything of it.

Taylor: Describe what your friends and family were saying.

Rob: When I first started using it, people looked at me like I was from mars. They were like, “Why would you do that?” I was like, “I live in a town of thirty thousand people and most of them are married, you know. So if I want to find somebody, this is what I've got to do." And so I did it. But I know there was a stigma to it. My friends thought I was crazy. And that was why I was so circumspect when I was putting my information out there because I wasn't comfortable doing it. But as I did it more, I got more comfortable with it.

Taylor: And describe your experience using the actual platform of, going through profiles and then actually going to meet these women.

Rob: You know, you can size them up fairly well. I say fairly well, because everybody misrepresents themselves and many of the women I went out with were nuts. So what you saw on paper was not necessarily how it turned out to be in real life.
Up to this point, Rob had been online dating for 10 entire years… So, as you can imagine, he was burnout to say the least, but his luck was about to change…
Rob: The funny part of all of this is that after being on, I had an account up until a few years ago, and it was literally down to the last day, and I thought, you know, “I'm done. I'm not going to renew this. This is bullshit. I'm tired of all the nonsense and driving all over the place and and not meeting anybody.”

And I thought, “Well, I'm just going to move.” I mean, that was my solution. “I'm going to sell my house. I'm going to move to my kids who are living in Austin, Texas. I’ll just move there and then there'll be lots of women to choose from.” Literally that last day of my account, I went online and I was just scrolling through potential dates and I spotted a picture of this beautiful woman who I didn't really know, but I knew who she was and was a friend of her now ex-husband. I said, “Are you kidding me? You're dating? Do you want to get together?” She lives literally one mile away, and we hit it off right away, and we've been together ever since.

The funny part is, after all of this, dating people as far away as Tulsa for crying out loud, I find this woman who I really like just a mile up the street. To make it even more coincidental; she just went on with a sample account for an hour. She was home sick one day and kind of in a feverish mood — and she's the last person in the world to ever put herself out there like that, but she did — and I just happened to see it in the one hour she was on and on the last day of my account!
Now we’ve gotten a glimpse into why online dating was exploding — it was actually working for people. Rob’s 10 years of online dating had finally paid off. Granted, it took a lot of hard work; like meeting tons of people that had misrepresented themselves in their profiles. After doing some digging on the Pew Research Centre, I actually found that an entire 54% of online daters felt that someone else seriously misrepresented themselves in their profile. So, I wanted to talk to one last person that could give me insight into what else people were experiencing with this new technology. Meet Jennifer, a 51 year old librarian living in Kenosha, Wisconsin. She started online dating in 2008 shortly after coming out of a divorce.

Online dating (2008)


Jennifer: Right away I knew that I didn't want to poach men at my kid's soccer games to meet people. So I pretty immediately went to online dating, which was only computers at that time. Nobody had smartphones. I can remember going into the office, logging on with dial up. It's so funny to think about. I think what I used was Plenty Of Fish, or maybe the first one I used was The first thing I had to figure out was there are some people who definitely want to just talk through messages like forever. I don't know what their story is, but when you're new, you're like, “Oh, I'm connecting!” and I would always wait for a guy to ask me out. But with some people, I was like, “This is never going to happen!” They just wanted a penpal.
After hearing Jennifer's story, I started looking into it. In fact, in 2005, only 43 percent of online daters had gone on a date with someone they met through an online dating site. That means that fifty seven percent of online daters weren't dating at all. They were essentially pen pals.
Jennifer: The second thing I had to figure out was how to meet somebody who actually wanted to date someone and have a relationship where you spend time doing other things than just having sex. Some people would be really straightforward. I mean, there's always like, you know, the bold sex seekers. Especially if they were a lot younger than me, they would say very funny things like “Do you like your feet licked?” would be their opening line.

Then there would be some men who they'd be like, “Yeah, I want a relationship.” And I think that for some they sincerely meant it. It's just that their notion of what a relationship is is just someone with whom you're only having sex and you're getting together and you're having sex and maybe a little conversation, and that’s just as far as their relationship capacities go. For some people, they just want to date someone for the rest of their life. You know, they don't want to live with someone or marry someone.

The person dating has the rudder for their dating life. So if you don't have a rudder, you're going to have even more wacky and disappointing experiences. I mean, I certainly won't have regrets that I didn't try and get myself out there. And these apps have given me a vehicle to do that. As a teacher in a female dominated career, mother of three in a town that I didn't necessarily feel like there's a lot of men for me, I've been very appreciative that it exists. Otherwise, what would I be doing? Ew, I don’t even want to think about it!
Online dating opened up the possibilities for many people, and served as a tool to meet singles they wouldn’t otherwise meet in their small social circles. It could be a significant aid for those that knew how to navigate the murky waters of online dating. But with each year that passed, the waters got a little bit murkier…

By 2010, fake profiles and scammers were widespread. A class action lawsuit filed in 2010 alleged that kept thousands of inactive and fraudulent profiles on the site to boost its numbers. And in 2015, the FTC reported that people lost $33 million dollars to romance scams. In one case, the victim of a scam describes how she was duped out of $2 million dollars by an online suitor she had never met.

Romance scam victim


Initially, he would read my wall, I would read his wall, we would post things, he would like things, I would like things. Then, it got to we would just share e-mails. We started sharing pictures. I knew that, just based on the conversations that we’ve had, that he was someone that I would like to meet. I felt a real soul connection with him right away. We sang to each other. We prayed with each other. We’d talk about what happened at church on Sunday.

There wasn’t an immediate talk about getting together. He was trying to finish up a job in California, and he needed some money to help finish that job up. And so I sent him [money]. I thought about it long and hard. I prayed about it. And I’ve always been a very giving person. And I figured if I had money in the account, that I could send him some money. And he promised to have it back within 24-48 hours. And I thought—I could do that, no one would ever know, and I’d be okay. But one thing kept happening after another. He’d need more money because he was coming in over budget. Things didn’t get done on time. He needed a lawyer. He had to take a money loan and it needed to be paid back.

Part of me thinks that he’s going to come through and pay me back what he owes me and, you know, swoop in here, be the knight in shining armor. But it’s just so absurd that there’s a big part of me that doesn’t believe that. And that is where this is all so pitiful is because, if he’s a scammer, I’ve been so brainwashed. And I’ve lost everything. It’s all I had. It’s any inheritance that I could have passed on to my daughter. The loss of money was my future and knowing that I wouldn’t have to work, that I could just make it to the ripe old age of whatever and be perfectly comfortable. The loss that I’ve suffered emotionally I think has even been more traumatic.

I can’t even imagine a man, a person, that could be this bad. So, I think of him—I can’t think of him that way. My mind keeps me from thinking of him that way because there can’t be a man in this world that could be this horrible to have purposefully done what he’s done to me. I don’t want this to happen to anybody else. If they’re real, and if the love is real, they are going to want to see you as soon as possible. I mean, it’s been two and a half years and I still haven’t seen his face.

This chilling story was becoming more and more common at the turn of the decade. But scams weren’t the only concern facing the rise of technology in the 2010s. When the decade began, tech meant promise. It connected us in ways we could barely imagine. But somewhere along the way, technology became an insidious part of our dating lives and relationships. What happened? You’ll have to wait for part 2 to find out…

Taylor Wade

Taylor is one of the founders of Ambiance Matchmaking. She now dedicates her time to curating content for our community through her podcast and blog. Writing and podcasting is the art of great story-telling. As a relationship writer and editor, she has always sought to capture the reality of the dating experience, full of drama, friction, and joy. The best mind is an open mind, so she specializes in asking questions and approaching a story without preconceptions.

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