Five Mini-Challenges to Make Going Out Alone Less Scary
Going out solo can feel intimidating—even downright terrifying. For many women, especially over 60, the idea of walking into a bar, restaurant, or event alone is enough to make staying home with Netflix and takeout sound a whole lot safer.
But here’s the truth: the only way to get more comfortable being out on your own is to practice it. Confidence isn’t built in theory, it’s built in action. That’s why I’ve created five simple “mini-challenges” designed to help you ease into solo outings. Think of them like training wheels: small, manageable steps that build up to real confidence.
Ready? Let’s go.
1. Have a Coffee Solo
Start small and casual. Take yourself to a cozy coffee shop, grab your favorite latte, and stay for at least 20 minutes. No laptop required. Just sit, sip, and people-watch. The goal here isn’t conversation—it’s simply learning to be comfortable in public without a companion.
2. Go to a Bar Early and Chat With the Bartender
Bars can feel intimidating when they’re crowded, so go early—when the place is still relaxed. Order a drink and strike up a short conversation with the bartender (they’re trained professionals at putting people at ease). This helps you break the ice without the pressure of mingling with strangers right away.
3. Attend One Event a Month
Pick something that genuinely interests you—a book talk, live music, art opening, cooking class, or lecture. When you go in with curiosity about the event rather than worry about the people, it takes the pressure off. You’re there to enjoy, and if conversation happens, that’s a bonus.
4. Give One Stranger a Compliment
This is a confidence hack. Whether it’s “I love your earrings” or “That jacket looks amazing on you,” a compliment is the easiest way to connect with someone. Most people respond with gratitude, and sometimes it opens the door to a longer conversation. The trick is to make it genuine, not forced.
5. Stay 30 Minutes Longer Than You Planned
Here’s where the magic happens. If you normally bolt after your drink or meal, challenge yourself to stay just a little longer. Often, that extra time is when conversations start, energy shifts, and you find yourself relaxing into the moment. Growth happens in the stretch.
The Bottom Line
Going out solo doesn’t mean braving a wild night out on your own right away. It means taking small, deliberate steps that train your confidence and expand your comfort zone. Each of these mini-challenges will feel easier the more you do them—and soon, you’ll find yourself walking into rooms with ease, ready to enjoy whatever the night brings.