THE GENERATION GAP: How Do Four Different Generations View Dating? Let’s Find Out

What do Vietnam, Letterman Jackets, pagers and 50 Shades of Grey all have in common? They’re all the common denominator for cultural differences that defined each generations distinct dating styles. I sat down with two Baby Boomers, who were navigating dating in the 1960s; two Gen Xers who were dating in the 1980s and early 1990s; two Millennials who and were dating in the 1990s and 2000s; and two Gen Zers who are currently navigating the world of “Netflix and Chill,” and “sliding into the DMs.” Through these conversations it became clear to me that each generation has a unique perspective on what exactly defines sex, dating and romance.  

Most people assume that dating has always worked exactly the same way, but I discovered that the people I spoke with from each generation told very different narratives. Throughout the conversations with each generation, I realized how much the deterioration of the family unit, the Sexual Revolution and the advent of technology have influenced dating and sex.

Question 1: What year were you born?

Respondent 1: 1949, 70 years old

Respondent 2: 1947, 72 years old

Respondent 3: 1970, 49 years old

Respondent 4: 1974, 45 years old

Respondent 5: 1981, 38 years old

Respondent 6: 1981, 38 years old

Respondent 7: 2000, 19 years old

Respondent 8: 2002, 17 years old

Question 2: What kind of technology influenced the way people in your generation dated?

Respondent 1, 70 years old: My family only had one phone line so my sisters and I would tie the line up all day and night. I would also write a lot of handwritten letters, especially when my husband was in Vietnam for a year.

Respondent 2, 72 years old: My sister and I were lucky because our mom and dad paid for us to have our own phone line so we could talk to our boyfriends that way, without tying up the phone line. There wasn’t much technology aside from that.

Respondent 3, 49 years old: Answering machines came out when I was in high school and it was the coolest thing ever. With answering machines, you didn’t have to worry about leaving the house to run errands and missing a call from your boyfriend. He could just leave you a message.

Respondent 4, 45 years old: Leaving messages on the answering machine became the really cool thing.

Respondent 5, 38 years old: I got my first pager in high school so that was always how my boyfriend would reach me. Or if I was running late for something I could call him on the payphone and let him know.

Respondent 6, 38 years old: I would call my boyfriend on my cell phone or email him.

Respondent 7, 19 years old: Right now the big thing is Tinder and dating apps like that. You can also use Snapchat or FaceTime to talk to people. It makes long distance relationships a lot easier.

Respondent 8, 17 years old: Most people will find girls they like on Instagram and message them or get their Snapchat to start talking to them.

Question 3: What are some ways that people would flirt or what kinds of romantic gestures were there?

Respondent 1, 70 years old: Slam books were the thing at my high school. You would start a book to pass around where you would answer questions like “who has the best eyes in the class?” or “who has the nicest smile?” and then other people in the class answer the same questions.

Respondent 2, 72 years old: Giving someone your senior ring or letterman jacket was the biggest one.

Respondent 3, 49 years old: Guys would give their girlfriends their letterman jackets, that was a big one. Or if you really liked someone you would make them a mix tape.

Respondent 4, 45 years old: Mix tapes are the main one I can think of. Or giving a girl your letterman jacket.

Respondent 5, 38 years old: I can’t really think of any big grand gestures.

Respondent 6, 38 years old: I can’t think of anything except just flirting in person like standing close to the guy you liked or touching his shoulder when you talked to him.

Respondent 7, 19 years old: Most flirting is just like Snapchatting someone a lot. Boys will tell you to hit them up if they want you to come over.

Respondent 8, 17 years old: There’s not really much flirting. You’ll just Snapchat the girls you like and hope they Snapchat you back.  

Question 4: How did your generation handle sex in relationships?

Respondent 1, 70 years old: People didn’t have sex outside of marriage. People didn’t talk to their friends about sex either, everyone was very private. You dated to get married and have children, so sex and intimacy were saved for that.

Respondent 2, 72 years old:  Nobody was having sex with anyone they weren’t married to. Women would occasionally talk to their friends about their sex lives but just brief mentioning of it, never any detail.

Respondent 3, 49 years old: Premarital sex was no longer something that would be considered taboo, but it was nothing like the culture surrounding sex today. You really only had sex with your boyfriend or someone you were in love with, not just any guy.

Respondent 4, 45 years old: Almost everyone I know was having premarital sex but they weren’t floozies. It was like you’d have sex with someone you’d been dating for a long time, if you were sure you were going to get married. You didn’t just sleep around.

Respondent 5, 38 years old: Pretty much everybody was having premarital sex. I lost my virginity at age 18 and told all my friends about it. Of course, I didn’t tell my parents until I was older, but nobody made a big deal of it. If you’d been on a few dates it was pretty normal to have sex with them.

Respondent 6, 38 years old: As far as I know everyone had premarital sex. You’d go on two or three dates and then sleep with them, that was normal. You’d talk to your friends about what you did and that was how people learned more about sex.

Respondent 7, 19 years old: Sex is kind of the reason people date now. There are some people who want to get married but most people approach marriage with the mindset that if it ends in divorce they can just start over. Everything is allowed nowadays.

Respondent 8, 17 years old: Everyone is having every kind of sex with whoever they want. Nothing like when my grandparents dated.  

Question 5: What are the pros and cons to how each generation dated?

Respondent 1, 70 years old: The Baby Boomers had a very limited dating pool so I guess that was a negative thing. I really think we had it right though, at least with the way boys and girls interacted. Boys still came to the door to meet the parents when they picked the girl up for a date. It was very sweet and innocent and much more intimate. I think Gen Z is lucky that they have access to social media to meet each other but many of them aren’t using it in the right way and it’s taking some of the personalization and intimacy out of dating for them.

Respondent 2, 72 years old: I don’t think any generation has had it totally “right” but I think that Baby Boomers and Gen X definitely did a better job at keeping romance in relationships and making dating feel more special. The social media the younger generations have access to certainly helps with connectivity and long distance dating but if it’s being abused to the point of having meaningless, emotionless relationships then what’s the point?

Respondent 3, 49 years old: I think my parents’ generation did a really good job of dating. I think we did a good job of dating too. My children are all Gen Z and I do worry about them. Dating is easier for them but marriage is harder and marriage is where it really counts. The divorce rates these days are crazy and of course I don’t want my children to get a divorce.

Respondent 4, 45 years old: Is it okay to say I think my own generation had the most pros? Gen Xers really had it right. Relationships weren’t solely focused on sex, which is good because sex is such a small percentage of the amount of time you spend with someone when you’re married to them. Sex is important but it shouldn’t be the focus. Dating for us was just about having fun together, going bowling, playing mini golf, drinking milkshakes or whatever and just getting to know everything about the person.

Respondent 5, 38 years old: I think my generation kind of ruined it for the younger generations. We wanted to get away from the idea of waiting until marriage but we took it too far and now it’s really hard for the younger generations to get back to the heart of the idea of waiting for someone you love. And Gen Z has it even harder than we did because they have all this technology. I like the way Baby Boomers dated because there was way more romance.

Respondent 6, 38 years old: I think Millennials did well because they made things more socially acceptable, but what came with that was also making things less special.

Respondent 7, 19 years old: It’s actually really sad because everyone acts like they love the freedom of having sex with whoever they want whenever they want but I think most of us hate it. It ends up leaving people confused and heartbroken and unfulfilled. Most people don’t want to admit it but I think the Baby Boomers and Gen Xers were onto something. There’s something really nice about writing handwritten letters to each other and going on real dates and not just focusing on when you’re going to get to have sex. I think most people come from broken homes now too, so marriage just isn’t really valued.

Respondent 8, 17 years old:Well I think the idea of picking a girl up at the door and meeting her parents is really nice. I don’t know why we don’t do that anymore. I think the older generations had more intimacy and romance and my generation is kind of lacking in that.

The consensus? As technology has advanced dating has become easier but the sacrifice made has been long lasting, meaningful relationships. Even Gen Zs agree, that as sex has slowly lost its value over time, dating has become less about intimacy and marriage, and more about personal freedom and exorbitant fleeting pleasure.