Dear Reader Who's Been Single for a While...
Wondering how to get back into dating after being single for a while? This advice column tackles the confidence questions we all have—from putting yourself out there and handling rejection, to navigating singles events and dating apps. Plus, practical tips on asking someone out (no matter your gender) and keeping first dates pressure-free. Because dating should be about connection and curiosity, not perfection.
ADVICE CATEGORIESFINDING LOVE
Fernanda
11/20/20255 min read
First of all, I see you. Being single for a long time isn't a bad thing—it can actually be really beautiful and necessary. But I also know that feeling when you're ready to open your heart again and your confidence feels like it's hiding somewhere you can't quite reach.
Here's the thing I want you to know: your confidence doesn't have to be perfect before you start. It builds as you go.
Start Where You Feel Comfortable
You don't need to jump straight into formal dates or dating apps if that feels too intense right now. Instead, think about places and situations where you can just be you and interact with people naturally. A hobby class, a book club, a running group, volunteer work—anywhere you can show up as yourself and have genuine conversations.
The beauty of these settings? You're not trying to impress anyone or perform some version of yourself. You're just being friendly, being present, and letting connections happen organically. And yes, you can absolutely be warm and interested in someone without slipping into the friend zone. The key is intention—if you feel a spark with someone, don't hide it. Let a little flirtation show through. Make eye contact. Smile. Show that you're interested in more than just friendship.
The Magic Moment: Asking Someone Out
Here's where it gets real—if someone seems interesting, ask them out. I know, I know, your heart is probably racing just reading that. But listen: you don't have to make it a big dramatic moment. It can be as simple as, "Hey, I've really enjoyed talking with you. Would you want to grab coffee sometime?"
That's it. No grand gesture required.
Now, I know traditionally men are expected to make the first move, but if you're a woman reading this? You absolutely can—and should—signal your interest too. Make eye contact, laugh at his jokes, find reasons to continue the conversation. If you're feeling bold, you can even ask him out directly. But if you've been giving clear signals and he's not responding? That's actually your answer. He might be interested in someone else, he might not be ready to date, or he might just not feel that spark with you. And as hard as it is, the kindest thing you can do for yourself is accept that and move on to someone who will light up when you walk into the room.
And if you're a guy and she says yes? Amazing! Now here's the thing about that first date: keep it simple and pressure-free. Coffee, a walk, maybe drinks or a casual dinner—something where you can actually talk and get to know each other. Don't plan an elaborate all-day adventure or an expensive evening that feels like an interview. Just create space to see if you enjoy each other's company.
Here's something really important I want you to remember: dating is about trying someone on for size, seeing if they fit into your life and you into theirs. It's not about going into every first date with loaded expectations about your future together, marriage, or whether this person is "the one." That's way too much pressure for both of you! Instead, approach it with curiosity. Do you have fun together? Do you feel like yourself around them? Do they seem genuinely interested in getting to know you? Those are the questions that matter on a first date.
Let's Talk About Rejection
Okay, so what if they say no? What if you put yourself out there and it doesn't work out?
Here's what I've learned: rejection isn't nearly as devastating as we build it up to be in our heads. Sure, it might sting for a moment. You might feel a little embarrassed or disappointed. But you know what? That feeling passes. Usually pretty quickly.
And here's what doesn't pass—the regret of never trying. The "what if" that lingers for months or even years. The wondering if maybe they felt the same way.
When someone says no, it's not a referendum on your worth. It just means they're not the right person for you right now. And honestly? That's valuable information. It frees you up to find someone who's genuinely excited about you.
The Real Confidence Builder
You want to know what actually builds confidence? Taking action despite the fear. Each time you put yourself out there—whether it leads to a date or not—you're proving to yourself that you're brave. You're showing yourself that you can handle uncertainty. You're practicing being vulnerable, which is actually one of the most courageous things you can do.
Your confidence will grow with each conversation, each smile you share, each time you choose to be open instead of closed off. It's not about being perfect or never feeling nervous. It's about doing it anyway.
Consider Singles Events (Yes, Really!)
I know what you might be thinking—singles events can feel a little intimidating or even cheesy. But hear me out: they actually take away so much of the anxiety that comes with dating.
Think about it. At a singles event, everyone there has already answered the two biggest questions: Are they single? Are they open to meeting someone? You're not left wondering if that person you've been chatting with at the coffee shop has a partner at home, or if you're misreading their friendliness as interest. Everyone's on the same page from the start, and that clarity is honestly such a gift.
Plus, there's something really freeing about being in a space where everyone knows why they're there. The pressure is lower because rejection isn't personal—it's just about connection and compatibility. And if you don't feel a spark with anyone? That's totally okay. You still practiced showing up, putting yourself out there, and having conversations with new people. That's confidence-building in itself.
If you've never been to one, I encourage you to give it a try. You might be surprised by how much easier it feels when the guesswork is already done for you.
And If You Want to Try the Apps...
Look, I'm not going to pretend that dating apps are perfect. We've all heard the stories—the ghosting, the poor communication, the feeling like you're being judged on the most superficial things. It can be frustrating, exhausting, and honestly kind of disheartening at times.
But here's the truth: some people do find real, meaningful love on apps. And it's not just because they got lucky (though luck never hurts). It's often because they're smarter "shoppers" on these platforms. They look beyond the obvious stuff—the perfectly curated photos, the height requirements, the checkbox lists. They read between the lines of profiles to find genuine personality. They ask thoughtful questions. They communicate with intention and honesty instead of playing games or sending one-word responses.
So if you want to give the apps a try, go for it! Approach them with an open mind and heart. Look for real humans, not perfect profiles. Start actual conversations. Be yourself in your own profile—let your personality shine through instead of trying to be whoever you think people want.
But also? Give yourself permission to step away if it starts feeling toxic or soul-crushing. If your experience turns sour, please don't let it make you give up on finding someone altogether. It might just mean that apps aren't the best method for you, and that's completely okay. There are so many other ways to meet people—ways that might actually be a better fit for how you connect.
You're Ready
I think the fact that you're asking this question means you already know you're ready. Your heart is nudging you forward. So trust that nudge. Start small if you need to, but start. Put yourself in situations where you can connect. Be friendly and genuine. And when someone catches your eye? Take a breath and go for it.
The world needs more people willing to be brave with their hearts. I have a feeling you're going to surprise yourself with just how strong and ready you actually are.
You've got this.
xo
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