Have you ever found yourself wishing that dating could be simpler, more direct, and—dare I say—more romantic than the endless swipes and quick texts we rely on today?
I know I have.
I often wonder if perhaps our parents’ or grandparents’ generation—often called “boomers”—knew something we’ve forgotten. They had certain dating habits that, if we’re being honest, sound pretty appealing in our digital-heavy age.
Let’s dig into ten of these old-school habits that I secretly (well, maybe not so secretly anymore) would love to see making a comeback.
1. Picking up the phone to call
I remember being a teenager and hearing my parents talk on the phone for hours. My mom always said she could tell everything she needed to know about a date just by how he spoke and listened during a call.
These days, it feels like every conversation happens through text. I’m guilty of it, too. But let’s be real: typing “LOL” doesn’t compare to hearing someone laugh in real time, does it?
There’s something incredibly personal about picking up the phone and letting the other person hear the warmth in your voice. It shows genuine interest and often offers a better sense of who you’re talking to.
I’m not saying we have to abandon texting altogether—it’s convenient, after all—but wouldn’t it be nice if a little more phone time came back into style?
2. Dressing up for a date
Back in the day, dressing up wasn’t about vanity; it was about showing respect for the person you were going to see.
My grandfather told me stories of polishing his shoes and wearing a crisp shirt before every dinner date he went on. It didn’t matter if it was a fancy restaurant or the local diner—it was the act of caring enough to look your best.
Now, I’m all for comfort (says the woman typing this in her favorite pair of worn-out jeans), but there’s a certain charm in making an effort.
When you take the time to pick out a nice outfit, it sends a message: “I value this date, and I value you.” And trust me, that’s a pretty strong message to send.
3. Planning a thoughtful date in advance
How often have you been on a date where the plan was decided while you were already on your way? I’ve had a fair few of those, and let’s just say, they weren’t exactly memorable.
Boomers tended to plan out the details—a reservation at a restaurant, a movie with tickets bought in advance, or even a picnic with a prepared basket of snacks. They’d pick you up at your door, map out how the evening would go, and often factor in a sweet little surprise along the way.
It wasn’t about being rigid or old-fashioned. It was about showing courtesy and reliability. As Stephen Covey once said, “Begin with the end in mind.”
While he was talking about leadership, it applies to dating, too: think through what you want the date to look like, and be intentional.
This habit took some of the awkward guesswork out of the experience, leaving more time to enjoy each other’s company.
4. Opening doors and other small gestures
Okay, let me be clear: this is not about men being dominant or women being incapable. It’s about thoughtfulness.
Holding a door open, offering your coat when it’s chilly, or walking on the traffic-facing side of the sidewalk might sound like clichés, but they’re really just sweet, protective gestures.
I know plenty of people who appreciate those little acts of courtesy because they say, “I’m thinking about you. I want you to be comfortable. I’m looking out for you.”
No matter who’s doing it for whom, these gestures can add a sense of warmth and care that seems to be fading in our instant-everything world.
5. Going “steady”
I’ve always been fascinated by how boomers would decide to “go steady.” It wasn’t complicated. You liked each other, you chose each other, and you said so.
Today, we navigate a minefield of “Are we exclusive?” or “Are we seeing other people?” conversations, often not knowing where we stand.
There was a refreshing clarity back then: if you were dating, you were together. No confusion, no trying to decode vague texts or awkward label-free situationships.
It might sound old-fashioned, but let’s be honest—clarity can be an incredible relief.
6. Writing love letters
A friend of mine once unearthed a box of letters her dad wrote to her mom when they were courting, filled with heartfelt words about how he felt in her absence.
Reading those letters, I was struck by how personal and meaningful they were. In an age where we can send a message in seconds, the idea of putting pen to paper seems almost unreal.
And that’s exactly what makes it so special. Putting your thoughts into long-form writing requires you to slow down, reflect, and be genuine. It doesn’t have to be Shakespearean sonnets—just sharing how you appreciate someone and what they mean to you.
There’s a quote by Dale Carnegie that goes, “When dealing with people, remember you are not dealing with creatures of logic, but creatures of emotion.”
Handwritten letters tap right into that emotional connection. They let the recipient know that you’ve taken time and effort to share what’s in your heart.
7. Giving undivided attention
Picture this: two people out to dinner, looking directly at each other as they talk, with no smartphones in sight. That’s how it used to be—there weren’t any gadgets to distract us, aside from maybe the occasional beep of a pager (if you remember those).
Now, I’m as attached to my phone as anyone, especially when I need to keep track of my son or check messages about work. But I still try to create phone-free pockets when I’m on a date. There’s a deeper connection that happens when you’re fully present with another person.
Research has found that having a mobile phone in sight, even if you’re not using it, can reduce the quality of a face-to-face conversation. So, maybe it’s time to put away the phone, even for just a couple of hours, and focus on the conversation unfolding in front of us.
8. Introducing dates to family
I’m not saying you should bring every potential partner to meet your family—let’s be sensible here. But I do miss the willingness boomers had to involve their loved ones once things were getting serious.
There’s something meaningful about bringing your partner around for a family dinner, letting them see where you came from, hearing your embarrassing childhood stories, and—if you have kids like I do—letting them see how everyone fits into the bigger picture of your life.
Yes, it’s old-school, but it offers a sense of acceptance and belonging that’s far more reassuring than any social media “relationship status” could ever be.
9. Saying it with flowers (or a simple token)
You might have read my post on making genuine gestures in a relationship, and I still stand by that advice: thoughtfulness goes a long way.
For many boomers, a small bouquet of flowers, a box of chocolates, or even a favorite book given at the end of a date was a normal courtesy. It was their way of saying, “I enjoyed spending time with you.”
Why not bring this back? A sweet token can be something as simple as a bookmark for the avid reader, or that specific brand of tea they once mentioned they love. The point is the gesture—showing you listen, you remember, and you care.
10. Perhaps most crucially: Being direct about expectations
One of the reasons I believe boomer relationships often got off to a better start is that they were more forthcoming about what they wanted—marriage, a steady partner, or just companionship.
Today, we tiptoe around the word “commitment.” We fear scaring someone away by being honest about our hopes and dreams too soon. We try to play it cool. But is playing it cool really worth missing out on a shared vision for the future?
I say no. When we’re upfront, we find out faster whether we’re on the same page or not. That can save a whole lot of heartbreak.
Wrapping up
When I think about how dating used to be, it’s not about nostalgia for the sake of it. It’s about recognizing that certain customs and courtesies can genuinely improve the way we connect.
Here at DM News, we believe in the power of small, intentional actions to transform our relationships and our lives. And while we can’t turn back time, we can bring back some of these habits in our own way.
Call more often instead of texting. Get dressed up just because you want to impress that special someone. Be honest about your intentions rather than leaving them guessing. If you feel inspired, write a letter—or at least a heartfelt note.
Real connection thrives on thoughtful gestures, open communication, and genuine presence. These are the things that make dating meaningful, no matter what generation you’re in.
So, let’s give these old-school habits a second chance. Who knows? We might just discover a new level of romance—and ultimately, deeper, more fulfilling connections.
