Dating apps are a double-edged sword—they can be an exciting way to meet new people, but they can also leave you wondering, “What the heck should I say now?”
Whether you’re just starting or swiped through hundreds of profiles, one thing’s for sure: messaging is a vital part of the whole process. It’s your chance to stand out, make a good first impression, and maybe even land a date.
So, how do you make your messages shine? Here are the do’s and don’ts that’ll help you master the art of messaging, from initiating the conversation to keeping it going.
The first message is your chance to grab someone’s attention, and a generic “Hey” just won’t cut it. Why? Because it’s boring. It’s easy, but it’s also a missed opportunity to show you’re genuinely interested.
Personalizing your message means showing you took the time to read their profile and pick up on something you have in common.
Example: if they mention they love dogs, start with something like,
“Your dog looks adorable! What’s his/her name?”
Or if they have a cool hobby listed, ask about it:
“You’re into photography? What’s your favorite subject to shoot?”
Personalization isn’t just about flattery—it’s about showing that you’re paying attention and want to get to know them.
One-word responses, or worse, completely ignoring a message, can make you look uninterested or dismissive. It’s like going to a dinner party and only saying, “Hi” and then just staring at your plate the whole time. Lame, right?
Instead, aim for more engaging responses. When they mention something about their day or a fun fact in their profile, don’t just say
“cool” or “nice”
Respond with something that keeps the conversation moving, like:
“That sounds like a blast! How was the rest of your day after the hike?”
This shows you’re interested in what they have to say and are open to building on the conversation.
You’re probably familiar with this—on most apps, it’s usually up to the guy to make the first move. If you see someone you’re interested in, why wait? Send the first message. Don’t make the mistake of waiting to see if they’ll message first—it can leave you stuck in the dreaded “Who’s going to text first?” game.
Taking the initiative doesn’t mean overthinking it. A simple, friendly greeting with a touch of personality goes a long way. You don’t need to recite Shakespeare, keep it casual and engaging. If they’re interested, they’ll respond. And if not, no biggie.
There’s always another match!
Flirting can be fun, but it’s also a delicate art. Coming on too strong right out of the gate—especially when you haven’t even had a real conversation yet—can be a huge turn-off. It’s important to balance your tone and avoid overly sexual comments, or too many compliments too soon.
Instead, build some rapport before you take it to the next level. You can still be playful, but make sure you’re respecting their boundaries. If they’re not engaging in the same type of flirting or humor, dial it back and give them space to respond how they’re comfortable.
A question like “Do you like music?” may seem innocent, but it’s the conversational equivalent of a dead end. A “yes” or “no” answer doesn’t give either of you much to work with. Instead, ask open-ended questions that can lead to a deeper exchange. Try asking:
“What’s the most unforgettable concert you’ve been to?”
“If you could only listen to one style of music forever, what would you choose?”
These types of questions show you’re genuinely curious about them, and they give the other person a chance to share something about themselves.
Open-ended questions also give you clues about what they care about, making it easier to build a deeper connection over time.
It’s tempting to keep firing off messages when you’re excited to talk to someone, but this is one of the fastest ways to overwhelm someone. If you send five texts in a row without giving them time to respond, you might seem desperate or, worse, come off as overwhelming.
Pace yourself. Think of texting as having a conversation in person. You don’t talk over someone, and you don’t talk too much. It’s all about balance. If you’re sending a message and anxiously waiting for them to reply, try to relax. You don’t need to bombard them with multiple messages. A well-timed response keeps things comfortable.
One of the key things to remember when messaging is to be true to yourself. It may sound cliché, but it’s the reality. You won’t win someone over by pretending to be someone else, no matter how smooth you are.
If you’re witty, be witty! If you’re shy, that’s fine—don’t feel pressured to be something you’re not just to impress them. People appreciate genuine, down-to-earth conversations over anything overly rehearsed. Plus, being authentic sets the stage for a more real connection down the line. The right person will appreciate you for you.
We’ve all seen them: the tired, overused pickup lines that are more likely to make you cringe than elicit a smile. Lines like:
“Are you a magician? Because whenever I look at you, everyone else disappears”
might get a laugh—but that’s usually because they’re so corny, not because they’re effective.
Instead, be original and thoughtful. A genuine comment about something in their profile, or a funny question related to something they’ve shared, is much more likely to spark a genuine conversation than a tired pickup line. Authenticity trumps the cheesy stuff every time.
Once you’ve started messaging and things are going well, keep the momentum up. Share fun facts, ask interesting questions, and keep it lighthearted. If you’ve found some common ground—maybe a love of hiking or similar taste in movies—use that as a jumping-off point for the conversation.
Don’t be afraid to take the conversation offline if it feels right. If you’re getting along and the conversation’s flowing well, suggest moving to another platform like Instagram, or even taking things to a real-life date. But don’t rush it. Enjoy getting to know each other first, and when the time feels right, take it to the next level.
Final Thoughts
Navigating the world of dating app messaging doesn’t have to be stressful. By staying genuine, respectful, and engaging, you’ll increase your chances of sparking meaningful conversations that could lead to something special.
Remember it’s all about balance. Initiate with confidence, but don’t go overboard. Respond thoughtfully, and always be yourself. If you follow these dos and don’ts, you’ll be well on your way to dating app success. Good luck out there!
Dating after 50 is like a treasure hunt—exciting, full of surprises, and occasionally, you might find yourself with a map that leads to a big pile of nope. Whether you’re looking for a genuine connection or a fun night out, sometimes you end up on a date that’s as uncomfortable as wearing a wool sweater in the middle of summer.
So, what’s the move when you feel that unease creeping in? How do you make a graceful exit—without having to fake a wild story about an imaginary cat needing emergency surgery? Let’s dive into how to exit a date safely and assertively, so you can live to date another day.
Recognizing When You’re Uncomfortable on a Date
First thing first: you need to know when the date is heading south before you find yourself locked into an uncomfortable situation. Sometimes, we ignore our gut feelings because we’re trying to be polite or give people the benefit of the doubt. But if your date is giving off serial killer vibes (or even awkward uncle vibes), it’s time to listen to that little voice inside your head. Some signs that things might be going south:
Inappropriate comments
If they’re asking you to rate your attractiveness on a scale of 1 to 10 or discussing their ex in detail, consider this a giant red flag. No one needs that kind of negativity in their life.
Unequal conversation
If your date talks about themselves for the entire evening while you barely get a word in edgewise, it's time to realize that maybe they’re more “interested in themselves” than “interested in you.”
The “creep factor”
You know that feeling when you get weirded out? Trust it. It’s like a sixth sense, but instead of detecting ghosts, it’s detecting bad dates.
Recognizing these signs early can save you from suffering through a two-hour dinner you’ll regret later. Your peace of mind is priceless.
Okay, you’ve realized things are a little off. Now, how do you get out of this uncomfortable situation without looking like you’re starring in a reality TV show exit scene? Here are some tips:
You don’t have to write a dissertation about why the date isn’t working. A quick, polite exit is all it takes. Just be firm and honest, but also remember: you’re not a bad person for deciding that this date isn’t your cup of tea. Try something like:
“You seem like a nice person, but I’m not feeling the connection. I think I’ll head out now. Thanks for the drink/meal/time, and I hope you have a great evening!”
“This has been fun, but I think we’re looking for different things. I’ll head out now, but best of luck with your search!”
Have an “Exit Strategy” (aka The Preemptive Escape Plan)
One of the keys to dating for women after 50 is knowing that you are allowed to leave when it’s not working. It’s not a crime, it’s self-care! And the best way to exit a date gracefully is to have a plan. Here are some strategies to consider before you even walk into the restaurant:
The “Safety Check”
Let a friend know where you’re going and when they should expect to hear from you. If you need to exit early, text them “HELP” or “Call me,” and you’ll have a perfect excuse to bail.
Set a Time Limit
If you’re worried you’ll get sucked into a never-ending conversation about their stamp collection (or something similarly thrilling), set a time limit. Let your date know you only have an hour. This gives you a built-in out, and they won’t feel rejected when you excuse yourself.
Having a plan is like wearing a seatbelt—it just makes sense. Plus, it saves you from getting stuck in an endless dinner with someone you’ll never see again.
Exit Gracefully Without Feeling Like You’re the Villain
Exiting a date doesn’t mean you have to feel like a bad person. Sure, it’s a bummer, but you’re doing yourself and your date a favor. No one should ever feel obligated to stay on a date that doesn’t feel right. Here’s how to leave without guilt:
Be polite but firm
You don’t need to apologize for wanting to leave. Just be courteous but direct. Think of it as gently closing a book you weren’t into—no need to throw it across the room.
Use body language
If you’re having trouble finding the right words, let your body language do the talking. Simple cues like gathering your things, checking your watch, or standing up can signal you're ready to wrap things up. If all else fails, pull the “Oh, look at the time!” move.
You’re not abandoning anyone—you’re simply acknowledging that this date wasn’t a good fit. And that’s okay!
Prioritizing Your Safety When Exiting a Date
If the date makes you uncomfortable in a way that feels unsafe, your exit should be as swift as possible. Your safety always comes first, no matter how awkward the situation may seem. Here are a few safety tips:
Stick to public places
If you’re meeting someone for the first time, choose a public location. It’s safer, and it’s easier to make a quick getaway if you need to.
Keep your own transportation
Having your ride is a must. If you need to leave suddenly, you won’t have to wait for a ride or rely on your date to get home.
Trust your instincts
If your gut says, “This is not good,” don’t argue with it. Your intuition knows when something’s off. And remember, it’s better to be safe than sorry.
If your date turns into a “nope” situation, don’t hesitate to leave quickly and without explanation. Your safety and peace of mind are worth more than any awkward moment.
Final Thoughts: Navigating Uncomfortable Dates with Confidence
Dating for women after 50 can be both exhilarating and a bit nerve-wracking, especially when you find yourself in an uncomfortable situation. But remember, you’re in control of your own experience, and it’s perfectly okay to exit a date that doesn’t feel right.
Whether it’s a polite but firm goodbye, a clever exit strategy, or prioritizing your safety, leaving an uncomfortable date assertively doesn’t have to be awkward or embarrassing.
So, take a deep breath, trust your instincts, and remember: there’s always a graceful way out of any uncomfortable date. Now go out there and date like the confident, savvy individual you are—just don’t forget to bring your “getaway plan.”
