10 Ways to Make Dating Fun Instead of Exhausting

So, you’ve dipped your toe back into the dating pool, and, surprise!, it’s more like a shark-infested ocean of cringe-worthy first dates, ghosting, and men who think sending a selfie from their car is “flirting.” We get it. Dating as a widowed woman can feel like running a marathon in high heels while juggling flaming swords. But don’t worry, we’re here to turn that dread into delight!

Here are 10 ways to make dating fun instead of a soul-sucking chore. Buckle up, because this ride is about to get interesting!

1. Stop Treating It Like a Job Interview

Yes, you want someone who doesn’t live in his mom’s basement, but interrogating him about his five-year plan before the appetizers arrive? Not fun. Instead, treat the date like an adventure, be curious, but let the conversation flow naturally.

2. Swipe Right on Yourself First

Before you start swiping on others, remind yourself why you’re a catch. Make a list of everything that makes you amazing. Confidence is the best dating app filter, trust me!

3. Set a ‘Weird Question’ Rule

Standard questions = boring. Instead, ask things like, “If you could only eat one meal for the rest of your life, what would it be?” or “What’s your guilty-pleasure TV show?” You’ll weed out the bland ones fast!

4. Laugh at the Awkwardness

Spilled your drink? Accidentally called him by your late husband’s name? Oops. Instead of spiraling into embarrassment, own it. Awkward moments make the best stories later.

5. Avoid the ‘Walking Resume’ Syndrome

You don’t need to list your accomplishments like you’re at a job fair. Let your personality shine through instead of treating the date like a LinkedIn profile in human form.

6. Date Outside Your ‘Type’

The guy who doesn’t fit your usual checklist might just surprise you. Maybe he’s got a killer sense of humor or makes the best margaritas you’ve ever had. Be open, you might just find a gem!

7. Plan Fun Dates, Not Coffee-Table Interviews

Dinner dates are great, but rock climbing, trivia nights, or taking a cooking class? Way more fun! Shared experiences help you bond faster than a stiff dinner conversation.

8. Take Breaks (Seriously, It’s a Game-Changer)

Dating burnout is real. If you feel drained, pause the apps and do something that brings you joy, spa day, girls’ night, or just binge-watching your favorite show. Then, come back refreshed!

9. Use a ‘Dating Buddy’ for Support

Find a friend who’s also dating and share hilarious (or horrifying) experiences. It makes the process less lonely, plus you’ll get great feedback when you can’t decide whether a text is flirty or just weird.

10. Let Someone Else Do the Hard Work for You!

Now, here’s the real game-changer: why do all the work yourself when there’s a smarter way? Enter Flirtly, the dating concierge service that screens matches, sets up dates, and even preps you so you can focus on the fun, not the frustration. Imagine having someone sift through the “Hey, beautiful” messages for you, dreamy, right?

Stop Overthinking & Start Enjoying!

Dating doesn’t have to feel like another full-time job. With these tips (and a little help from Flirtly), you can actually enjoy the process again. Ready to date without the headache? Check out Flirtly now and make dating exciting again!

What’s been your funniest (or weirdest) date experience? Drop it in the comments below!

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