365 Squarey Monsters: Love, Rewritten: What Valentine’s Looks Like Today

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A lifetime in the flower-and-gifts business offers a unique vantage point. You see holidays evolve, rituals take root, and new ways of expressing love emerge. Taken together, these shifts tell a larger story — not just about relationships, but about where we are as a society.

Valentine's is especially revealing. Gifts are being sent earlier than they used to be, and nearly half are now intended for people outside of romantic relationships. In fact, watching that shift over time inspired last week's Celebrations Pulse on how Valentine's has become its own season.

Of course, romantic love remains an essential part of the story. What's changed is the way we use the season to express love more broadly.

That growth in the scope of Valentine's comes into focus in the stories readers have shared in recent weeks. The notes filling my inbox return to the same idea: Valentine's is an opening to reach out and show up for all the people who matter in our lives.

An expanding circle of love

Cathy wrote about one Valentine's spent working full-time as a registered nurse and studying for an advanced degree, all while her mother was in a nursing home. During that period, Cathy's husband, Charlie, made sure her mother received flowers and company. As Cathy put it:

"That loving gesture he extended to my mom meant more to me than all the roses, chocolates, and expensive gifts that a wife could dream of."

Another nurse, Katie, shared that she hands out Valentine's cards to her patients throughout the day. "It's a little thing," she wrote, "but I love bringing a bit of joy and levity to the people I care for."

Sally, a patient at a nursing home, wrote to say she buys several big boxes of Cheryl's cookies and shares them with her aides and staff members. She added:

"Everyone loves them. One person mentioned they sell them for Easter and summer, which I already knew. I think that was supposed to be a BIG hint for me to send more!"

I love those kinds of hints!

Celebrating love at home

Many of the Valentine's stories point to the fact that some of the most enduring expressions of love begin at home, in the ways parents and grandparents care for those around them, set examples, and create rituals that stay with us long after childhood ends.

I was reminded of that idea in a recent conversation with Kelly Williamson, an executive at the global advisory firm APCO . Kelly began with a story about her father. Every Feb. 14, for as long as she can remember, he has sent her flowers. The card always read, "From the man who loves you most." When Kelly got married, the message changed. Her father began signing it simply, "I love you — Dad," explaining that the original line now belonged to her husband.

That same thoughtfulness appeared in a note from Kate, who wrote about her father sending Valentine's cards not only to her but to her children as well. As a single parent, the gesture reminded her that she and her kids were seen and supported.

Terrie shared a similar reflection about her father, who remains her first call when she needs advice. She said his consistency continues to guide her.

The lighter side of the season

Some Valentine's memories earn their place by making us smile, reminding us that love often shows up in a willingness to roll with whatever the day brings.

Ursula shared a story that has become family legend. On a snowy Valentine's Day in Chicago in 1961, she was nine months pregnant and wondering what to give her husband when labor suddenly began. The day ended with the arrival of their baby girl!

Other readers leaned into playfulness. Linda described turning Valentine's Day into a full family event, complete with Valentine's Bingo, dollar-store prizes, pizza, and her signature homemade chocolate pie. The point, she explained, was to create a memory everyone could share.

Sandy shared plans that struck a similar note: a surprise breakfast, a casual dinner out, red and pink carnations on the table, and Valentine's cookies or cake to end the day.

In this week's Power & Impact, I sit down with Kelly Williamson, a senior executive at the global advisory firm APCO, to talk about what actually sustains a career and a company when the world keeps rewriting the rules.

Kelly shares her path from intern to executive and why trust and relationships have mattered more than any five-year plan. We discuss leading through uncertainty, navigating AI-driven and geopolitical change, and why empathy, values, and critical thinking are no longer viewed as soft skills, but as essential leadership skills.

The discussion spans the future of work, the disappearance of traditional entry-level roles, and what young people need to learn now for jobs that don't yet exist. Kelly also explains how leaders who stay grounded in their values are better equipped to guide teams through disruption.

If you're leading a team, hiring talent, or rethinking what a "career path" even looks like today, this conversation offers clarity and a reminder that in a fast-moving world, relationships still matter most. I'd love to hear your thoughts.

A note to reluctant Romeos

While Valentine's has grown beyond its focus on traditional romance, that expansion hasn't come at its expense. Romantic love still matters, and it deserves its place on the calendar — and in our lives.

I recently spoke with Arthur Brooks, one of the leading voices in the science of happiness. He reminded me that a happy life is never built alone; it grows out of finding someone you can build a meaningful relationship with.

One of the biggest mistakes, he says, is spending too much energy chasing numbers: a better title, a higher salary, the next milestone. Too often, that chase becomes an excuse for postponing commitment until "later."

So here's a thought, especially for those of you in your early 20s: If you've already met someone you can imagine building a life with, why delay it on purpose? Those early years matter. They're where shared memories are made, inside jokes are born, hard lessons are learned, and trust begins to take root. All of it compounds over time.

Love isn't just a spark, but a flame you tend over time. The sooner you care for it, the more warmth it can give.

50 Years In: A message for right now

As 1-800-Flowers.com marks its 50th anniversary, I've found myself thinking less about milestones and more about moments — the small, human ones that explain why our story is still being written. I'll be sharing reflections throughout the year, and this Valentine's story feels like the right place to begin.

A few years ago, while walking through the office and listening in on customer service calls, I overheard a conversation that has stayed with me ever since. A customer was trying to decide the best time to send Valentine's roses to his wife.

Like this year, Feb. 14 fell on a weekend. Should the flowers go to her office a little early? Or should they be delivered to their home? If they went early, what should the message say? After talking it through, the agent made a simple suggestion: "I couldn't wait until February 14th to send this to you. I love you so much."

The customer loved the idea. And so did I.

That line captured Valentine's at its best. Instead of focusing on a date on the calendar, it revealed the impulse behind it — the instinct not to wait, to say it now, and to reach out while the moment is real.

The right flowers deserve the right outfit

What's better than giving her flowers? Wearing the right outfit when you do. This Valentine's season, we're teaming up with Original Penguin to give a few lucky followers the chance to win gift cards for roses and the fit to do it in style.

You'll see that pairing come to life in the real world, too. All this week, bouquets will be popping up in Original Penguin retail stores, turning everyday shopping trips into fragrant reminders that the best Valentine's gestures don't have to be complicated.

To enter for a chance to win one of three prize packages, visit this post on Instagram, like it, and tag a valid account in the comments. Be sure to include #1800flowersPerryEllisSweepstakes in your comment.

Each prize package is valued at $200: a $100 Savings Pass from 1-800-Flowers.com and a $100 Original Penguin gift card.

Where has kindness shown up for you?

Next Sunday, Feb. 17, is Random Acts of Kindness Day. I love the idea of setting aside time to remind ourselves to be kind — especially to people we don't know. I've seen how even the smallest gesture can create ripples that travel much farther than we expect.

As I prepare next week's Celebrations Pulse, I'd love to hear from you about how kindness has shown up in your life. Maybe it was a stranger who stayed with you after a car broke down, a neighbor who arrived with a meal when words weren't enough, or someone who covered your coffee, wrote an unexpected note, or offered help at a moment when you weren't sure how to ask.

Please share your stories of kindness for next week's letter. You never know: Your experience might be the spark that encourages someone else to pass kindness along.

Worth watching: The power of a good team

I recently watched 49ers legend Joe Montana on CNBC as he shared a preview of his upcoming Worth magazine cover story and reflected on the team he's been building in venture capital.

What stood out was how much Joe's thinking about team-building has stayed with him across the chapters of his life. He talked about assembling partners with care and taking time to see how people work together before making long-term commitments.

The Worth cover story looks at how Joe has applied the same fundamentals he learned earlier in life to a very different arena. Whether on the field or in business, his focus remains on building teams deliberately and staying close enough to support one another when it matters.

As chairman of Worth Media Group, I'm incredibly proud of the team that brings the magazine to life and honored to feature Joe on our cover. His story is a reminder that strong teams are built deliberately, both in sports and in business.

Sunday, February 8, 2026

Love, Rewritten: What Valentine’s Looks Like Today

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