Lisa O
Dating has changed more in the last few decades than it did in the previous century. What once felt like timeless advice now feels outdated, awkward, or even counterproductive. Boomers may have grown up with a strict set of unspoken rules about love—but many of those don’t hold up anymore. Here are 15 boomer-era dating rules that just don’t make sense in today’s world.
Men should always pay for the date.
This rule was once seen as a gentleman’s gesture. Now, it’s more complicated. Many people prefer to split the bill or take turns paying. Sticking strictly to this rule can feel forced, especially if both people are financially independent. It also sets up a dynamic where generosity is expected instead of appreciated. Equality, communication, and mutual respect are now more attractive than rigid roles.
Don’t sleep together too soon.
Boomer wisdom warned that intimacy too early would ruin the relationship. Today, people understand that physical connection is just one part of compatibility. For some, it happens early and works out fine; for others, it takes time. What matters now is communication, consent, and mutual comfort—not following an invisible clock. There’s no universal timeline, and judging others for theirs feels out of step.
Always play hard to get.
This one might’ve worked in an age of handwritten letters and limited options. But in today’s world of instant messages and dating apps, it’s more likely to frustrate or confuse someone. If you’re interested, just say so. Playing games can backfire quickly, especially with people who value openness. What once created intrigue now often just kills momentum before things even start.
You need to be married by a certain age.
Back then, there was a timeline: finish school, get married, buy a house. However, modern relationships don’t follow that pattern. Some people marry young, others never marry, and many find love later in life. Putting pressure on yourself because you’re “behind” by boomer standards doesn’t help. Love doesn’t follow deadlines anymore—and happiness doesn’t depend on hitting some imaginary milestone.
Never date someone with baggage.
Boomers were raised on the idea that your partner should come with a clean slate. But that’s unrealistic now. Most people carry something—past relationships, kids, career changes. These don’t make someone less worthy of love. In fact, how someone handles their experiences can show emotional maturity. Avoiding anyone with “baggage” might mean missing out on the kind of depth that only comes from lived experience.
A man should always make the first move.
This rule discouraged women from showing interest for fear of seeming “too forward.” But today, that thinking feels limiting. Confidence is attractive, regardless of gender. If you like someone, it’s okay to speak up. Waiting for the other person to act can lead to missed opportunities and misread signals. Initiative is no longer a man’s job—it’s simply part of being honest and engaged.
Your partner must meet all your needs.
Boomer dating often painted romantic partners as all-in-one providers: best friend, soulmate, emotional anchor. But expecting one person to fulfill every role sets the stage for disappointment. These days, people understand that healthy relationships allow room for outside friendships, interests, and growth. A good partner enhances your life—but they shouldn’t be your entire world.
Don’t move in until you’re married.
Living together before marriage was once taboo. Now, it’s practical and often encouraged. Sharing a space helps couples understand compatibility in day-to-day life. It’s not about disrespecting commitment—it’s about building it with real information. Waiting until after marriage to discover you can’t live together peacefully isn’t romantic—it’s risky. This rule is more about outdated stigma than solid relationship advice.
Stay with someone because they’re “a good catch”.
Boomers were told to lock down a stable, respectable partner—even if love wasn’t fully there. Today, that thinking feels hollow. Being with someone just because they look good on paper rarely leads to happiness. What matters more now is emotional connection, mutual support, and shared values. A “good catch” is only worth it if they’re good for you.
Don’t talk about past relationships.
Boomers were taught to leave the past in the past. But today, people appreciate honesty. Talking about what worked or didn’t in previous relationships helps set clearer expectations. It’s not about reliving heartbreak or comparing partners. It’s about learning what shaped someone and how they show up in love now. Avoiding those conversations can feel like avoiding emotional depth.
Don’t ask them out first.
Waiting around used to be a strategy to appear modest or desirable, especially for women. But today, it just wastes time. People appreciate confidence and directness. If you’re interested, there’s no harm in saying so. Playing coy can come off as disinterest or immaturity now. The dating world rewards those who take initiative instead of sitting back and hoping to be chosen.
Always dress to impress on the first date.
While looking presentable is still important, rigid expectations about appearance have softened. Wearing a suit or a cocktail dress isn’t mandatory. Comfort and authenticity often matter more. Today’s dating culture values being yourself over looking like a polished version of someone you’re not. People now prefer someone who feels real—wrinkles, sneakers, and all—over someone who’s trying too hard.
Avoid serious topics like politics or religion.
Boomers were often told to keep first-date conversations light. But today’s daters want substance. Conversations about beliefs, values, and big life questions help people assess compatibility early on. While tact is still important, dodging meaningful topics altogether can feel shallow. Openness leads to stronger connections—and we’ve learned that it’s better to find out early if someone’s worldview just doesn’t click.
Marry someone from the same background.
Old advice pushed the idea that shared culture, class, or religion were necessary for stability. But now, diversity in relationships is not only accepted—it’s embraced. People from different races, countries, and belief systems form strong, loving bonds every day. What matters now is shared respect and emotional alignment, not checking off demographic boxes that used to define ‘suitability.’
If it’s not working, stick it out.
Boomers were raised in an era where staying together was the goal, no matter what. Divorce was stigmatized, and ending a relationship was seen as failure. Today, we know that walking away can be a sign of growth. People now value emotional well-being over longevity. It’s no longer about sticking it out—it’s about choosing joy, even if that means letting go.
