Dating can be quite a hard task, especially if you haven’t been in a relationship for a long time.
Maybe you’ve been busy building your career, raising kids, or binge-watching every single series on Netflix (no judgment here), or are still worried about the PTSD of your last affair.
But now, you’re ready to dip your toes back into the dating pool.
The water looks a little different from the last time you swam in it, and there are apps, ghosting, and people using avocado toast as a personality trait.
But fear not, that’s why I’m here!
How to Start Dating Again After a Long Time
1. Dust Off Your Charm and Confidence
First things first, remember that charm you used to have?
The one that could make anyone laugh and maybe even get a free drink or two?
Yeah, it’s time to bring that out of storage.
Confidence is key, even if you haven’t dated in a long time.
You don’t have to be the smoothest operator in the room; just be yourself.
And if your “self” happens to include dad jokes or a laugh that sounds like a car trying to start, embrace it.
Authenticity is attractive.
Imagine you’re at a party, someone asks about your long hiatus from dating, and you casually respond, “Oh, I was just waiting for the perfect moment… like a fine wine, I needed to age a bit.”
See? Instantly charming and a little bit mysterious.
Plus, it’s better than saying, “I’ve been busy re-watching ‘The Office’ for the 20th time.”
It can be nerve-wracking to get back into the dating scene after a long time, but everyone has their own insecurities and fears.
Embrace yours, and don’t try to hide them. This will only make you more relatable and endearing.
Just be genuine and let your personality shine.
2. Update Your Look, But Keep It Real
Let’s talk about your look. No, you don’t need to morph into a fashion icon overnight.
But if you’ve been rocking the same haircut since high school, maybe it’s time for a little refresh.
Consider it a fun adventure, like trying a new flavor of ice cream.
You might find that a new style makes you feel more confident.
No need to go overboard—this isn’t an episode of Extreme Makeover.
Here you are, going on your first date, looking like a whole new person.
Your date is like, “Wow, I didn’t know Ryan Gosling had a twin!” Okay, maybe that’s a stretch, but you get the point.
The goal is to feel good and look like yourself, just a polished version.
3. Learn the Modern Dating Lingo
Welcome to the future, where dating involves more swipes than conversations.
If you’re not familiar with the latest dating lingo, it’s time for a crash course.
Words like “ghosting,” “breadcrumbing,” and “benching” aren’t just terms from a horror movie.
They’re real things that happen in the dating world.
It’s like a bizarre game show where the prize is either a second date or a lifetime of awkward text messages.
Think of it as learning a new language.
If someone says they’re “ghosting,” don’t look for Casper; just know they’re not interested.
And if you hear “benching,” they’re not asking you to help them work out; they’re just keeping you on the back burner.
The more you know, the less you’ll freak out when it happens.
4. Get On the Dating Apps With Caution
Yes, dating apps are a thing now, although I wouldn’t encourage using them.
If you have to, be careful.
Dating apps are like the modern version of meeting someone at a bar, but with less alcohol and more selfies.
Setting up a profile can feel like crafting the perfect bio, which is like creating a resume, but instead of listing your job skills, you’re highlighting your best qualities (and praying someone finds them attractive).
Just keep in mind that your profile should be a reflection of who you are.
If you love hiking, mention it. If you’re a dog person, say it.
And please, for the love of all that’s holy, avoid clichés like “I love to laugh” or “I’m looking for my partner in crime.”
We all love to laugh, Karen and most of us aren’t trying to start a heist.
5. Practice Flirting Again
If it’s been a while since you last flirted, you might feel like a rusty bicycle trying to go uphill.
But don’t worry; flirting is like riding a bike, and you never forget how to do it.
Maybe you should take off the training wheels this time. Start small.
Compliment your barista, make a joke with the cashier, or wink at a stranger (but not in a creepy way).
The trick is to be playful and light-hearted.
Think of it as a game of ping-pong, where you’re just bouncing the conversation back and forth.
If you say something awkward, laugh it off. Everyone loves someone who can laugh at themselves.
And if they don’t laugh with you, well, their loss.
6. Prepare for the Awkward Moments
Let’s be honest for a second. There surely will be awkward moments.
Maybe you’ll accidentally call your date by your ex’s name, or perhaps you’ll spill wine all over your shirt. It happens to the best of us.
The key is to embrace the awkwardness. Turn it into a funny story to tell later.
“So there I was, covered in Cabernet, looking like a crime scene, but hey, at least I was memorable!”
If your date is awkward, too, it’s a good sign.
It means they’re human, not a dating robot sent to test your patience.
Bond over the awkwardness and use it as a softener.
Sometimes, the most embarrassing moments are the ones you laugh about later, trust me.
7. Set Boundaries and Know What You Want
Just because you’re diving back into dating doesn’t mean you should settle for anything less than you deserve; take a very good note of that.
Be clear about what you want, whether it’s a casual fling or something more serious.
And don’t be afraid to communicate your boundaries.
If you’re not into texting all day, let them know. If you hate pineapple on pizza, stand your ground.
Remember, you’re a catch. Don’t let anyone make you feel otherwise.
You’ve been living and doing your thing, and now you’re ready to share it with someone.
But that someone should be worth it.
No one deserves to be treated like a second choice or a placeholder.
8. Have Fun, and Don’t Take It Too Seriously
Dating can be a rollercoaster of emotions, but it’s also supposed to be fun, isn’t it?
So, don’t get too caught up in the what-ifs and the maybes.
Enjoy the process, laugh at the ridiculous moments, and be open to new experiences.
If you’re nervous, remember: the worst thing that can happen is a wrong date.
And even then, it’s still a good story. You can always laugh about it with your friends later.
Date Yourself Too
Before you dive into dating others, make sure you’re also dating yourself.
Treat yourself to nice dinners, take yourself on movie dates, and buy yourself flowers.
When you’re happy and content on your own, it’s easier to attract someone who complements your life instead of completing it.
In the end, dating is just another adventure.
It’s a chance to meet new people, learn about yourself, and maybe, just maybe, find someone who’s as awesome as you are.
So, put on your best outfit, flash that killer smile, and get out there.
The dating world is your oyster, and you might find your pearl.