14 Solo Date Ideas & The Truth About Feeling Lonely on Valentine’s Day

Welcome to February, the season of love.

For some, this month is filled with shared moments of appreciation with a partner. For others, it’s about friends, community, or family. And for some, it may quietly bring up feelings of loneliness.

Here’s the thing: I love love.

I love showing appreciation. I love watching someone’s face light up over the smallest gesture. I love deep connection, the kind where you feel seen, understood, and safe enough to be vulnerable. Growing through hard seasons together, encouraging one another to chase dreams, and witnessing how love softens, deepens, and evolves over time.

I see love in the small things too: The way your dog greets you like you’re their whole world the moment you walk through the door, quiet smiles shared between strangers, a phone call from a friend just to check in, letting the sun warm your face for a few still moments. I see it in older couples still holding hands, their love shaped by years of choosing each other, again and again.

Love is beautiful.
And yes…it can hurt.

But it’s also everywhere, if you’re willing to slow down and look for it.

So if you’ve recently gone through a breakup, or this season feels heavier than usual, I see you. Truly.

For me, it’s not that I’m unhappy on my own. It’s noticing the subtle ways I still miss having someone. The small reminders that pull you back into a memory. The moments where you think you’re “over it,” only to realize healing isn’t linear, as they say, it’s often one step forward, three steps back.

And that’s okay.

It’s okay to be comfortable on your own and still miss closeness.
It’s okay to feel joy and sadness at the same time.
It’s okay to let yourself cry, as long as you keep taking that one step forward.

So this month, I have decided to love myself a little extra.

Even though I spend a lot of time alone, I realized it’s been a while since I’ve gone on a date. And while I’m not ready to date someone else, I am ready to be intentional with myself.

So in the spirit of Valentine’s Day, I’m taking myself on 14 first dates.

Getting comfortable in your own company matters, whether you’re single or in a relationship. But if you’re in a season of feeling lost, lonely, or unsure of who you’re becoming, learning to enjoy your own presence is essential. If you wouldn’t hesitate to do something kind for someone else, don’t you deserve that same care, if not more?

Now, you might be thinking: “I already spend time alone. I’m happy on my own.”
And that’s beautiful.

For me, though, this is about doing something different. Stepping outside routine. Creating moments that feel intentional, fun, and slightly uncomfortable. Yes, romanticizing the everyday is powerful, but sometimes we also need novelty. A little spark. A reminder that life gets to feel expansive.

So here is my list of 14 First Dates… with yourself

1. A long beach walk with a warm drink + journaling

2. Buying myself flowers and arranging them

3. Trying something new (surfing, dance, anything I’ve been curious about)

4. A café date to write a letter to my future self

5. A pottery class to challenge my creativity

6. A solo picnic

7. Pilates at a new studio I’ve never tried

8. At home spa! Take a bubble bath, put on an eye mask, light an incense, put on your cozy set, meditate (or try a yin yoga class)

9. Taking myself out for dinner

10. Visiting a bookstore, buying a novel, and reading

11. Cooking a fancy meal for myself or trying a cooking class

12. Volunteering my time at an animal shelter

13. Go to a market, browse all the vendors and pick up a little treat!

14. Planning a future trip, writing out my bucket list or setting future goals

Think of this as a social experiment, an opportunity to learn what you enjoy, what lights you up, and who you are becoming. The key is presence. Put the phone down. Let yourself experience the quiet, learning to enjoy your own company is part of the experience.

On social anxiety

This is often the biggest reason people avoid solo dates. We worry about being judged, about what others might think. But the truth? Most people are far more focused on themselves. And the confidence you build by showing up alone is unmatched.

If solo dinners feel intimidating, bring a book or journal. Or start with activity based dates, something that keeps your mind engaged and grounded. This definitely helped me at the start!

On self-discovery

Reconnecting with yourself happens through exploration. Treat this like play. Learning you don’t like something is just as valuable as learning you do. Journal after each date. Notice how you feel. New experiences spark creativity, awareness, and appreciation.

On healthier relationships

We can’t fully show up for others until we show up for ourselves. When you nurture your relationship with yourself, every other relationship benefits. You become more grounded, secure, and open.

If this season feels heavy, remember: solo dates aren’t about loneliness, they’re about embracing your own company. You are literally the one relationship you’ll have for your entire life. So you may as well pour all your love back into yourself!

The sooner you learn to love yourself, the more life opens up.

And if no one has told you lately, I love you.

Xo.
Cass

P.S. (If you spot a spelling mistake, even with spellcheck, let’s call it character… it was written from the heart, not perfection)