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Tiff Baira is New York City's official TikTok Cupid, loved by hundreds of thousands for her confidence-boosting content. She's the host of Take Me Out, where she teaches the art of dating, and Street Hearts, where she serves as a global matchmaker. Tiff offers smart, practical advice to help you find love while staying true to yourself and embracing self-love every step of the way.
Introduction 1
Part 1: Getting into the Modern Dating Game 5
Chapter 1: Modern Dating: Has Romance Turned into Horror? 7
Chapter 2: Tinder, Hinge, Bumble, Oh My! Navigating the Dating Apps 17
Chapter 3: Finding Love While Loving Yourself 29
Chapter 4: Deciding to Date - Setting Standards and Having a Solid Dating Blueprint 39
Chapter 5: Resetting Your Dating Mind: Breaking the Rules and Building Your Own 47
Part 2: Meeting Someone and Setting Up a Date 51
Chapter 6: Flirting 101: The Flirtation Formula to Get 'Em Hooked 53
Chapter 7: No Wi-Fi Needed: Where and How to Meet People in Person 69
Chapter 8: How to Ask for or Reject a Date Invitation 77
Chapter 9: Right Place, Right Vibe: Nailing the Perfect Date Location 97
Chapter 10: Plan with Caution: Spotting and Avoiding Red Flags When Setting Up a Date 105
Chapter 11: Who's Got the Bill? Navigating the Check Etiquette 111
Part 3: Swipe Right to Date Night: The Ultimate GRWM Playbook for Your First Date 127
Chapter 12: From Outfit to Attitude: Making a Great First Impression 129
Chapter 13: Bye-Bye Butterflies: How to Crush First Date Nerves and Boost Your Confidence 139
Chapter 14: Big Date Energy: Starting and Keeping the Date Fun and Flirty 151
Part 4: Date or Fade? What Happens after the First Date 169
Chapter 15: Making the Most of Date Number Two and Beyond 171
Chapter 16: Ghosts, Goodbyes, and Getting Over It: Surviving the Heartbreak 185
Chapter 17: Beyond Small Talk: Asking the Questions That Really Matter 203
Part 5: Romance, Rewritten: Loving and Dating on Your Own Terms 221
Chapter 18: No Pressure, Just Pleasure: Navigating Sex in the City 223
Chapter 19: Second Chances: Thriving in the Dating World Post-Divorce 233
Chapter 20: Out and About: Navigating the LGBTQIA+ Dating Scene 243
Part 6: The Part of Tens 259
Chapter 21: Ten Things to Tell Yourself Before and After a Date 261
Chapter 22: Ten Red Flags to Avoid at All Costs 265
Index 273
Chapter 1
IN THIS CHAPTER
Feeling your way through the modern dating landscape
Knowing which rules and advice to follow and which ones to avoid
Figuring out how to date in the modern age and actually enjoy it
From ancient times, finding love has never been a straight path - more like a chaotic obstacle course with questionable detours. People went to war for love, wrote tragic poetry, and we got stuck with Romeo and Juliet as the ultimate romantic standard (even though, let's be real, they knew each other for three days and it ended in a double suicide). Fast forward, and here we are - post-pandemic, chronically online, and swiping like our thumbs are training for a marathon.
At this point, many of us have a stronger relationship with dating apps than with the people on them. Ghosting is a national pastime, "talking stages" last longer than some marriages, and somehow, despite having more ways to connect than ever, we're in a loneliness epidemic. What happened to the clarity of old-school dating? Courtship, love, marriage - it used to be a simple formula. Now, we're out here navigating rosters, what are we talks, and situationships so vague they could be the subject of a philosophy class.
But here's the deal: The old rules no longer apply, so it's up to us to create new ones that actually work. It's time to stop clinging to outdated timelines, stop trying to fit love into a perfect mold, and start figuring out what we actually want. Whether it's redefining commitment, dating for fun, or just trying to survive yet another Hinge voice memo introduction, let's dive into the madness that is modern love - chaos included.
If you've ever felt like dating today is a social experiment designed to test your patience, your self-worth, and your ability to decode mixed signals - congratulations, you are not alone. Dating used to be about finding someone you connected with. Now, it's about not getting played. Red flags? We spot them from a mile away but sometimes still ignore them because they have great hair. Some common modern dating traps include
The key to surviving? Recognize the games early, set your standards, and don't waste time on people who bring more confusion than connection. The following sections break down the absolute chaos that is the modern dating scene and explain how we can make it work without completely losing your sanity.
Situationships are basically the modern version of purgatory. You like each other, you spend time together, you might even meet their dog - but there's zero commitment. It's fun until you realize you've been in one for two years and you're still "just seeing where things go."
The difference between a relationship and a situationship? Consistency, clarity, and actual plans for the future. If you're stuck in something vague and they "don't like labels," ask yourself: Are you okay with that, or are you just afraid to leave because you don't want to start over?
Gone are the days when defining a relationship was a normal milestone. Now, we're out here trying to make "exclusivity" happen like it's some rare unicorn. The longer you avoid "The Talk," the messier it gets. If you're confused about where you stand with someone, ask yourself:
You deserve clarity, and the right person won't leave you hanging in uncertainty.
Having a "roster" is the modern version of keeping your options open. But at what point do options turn into distractions? Dating multiple people at once can be fun, but if you're constantly cycling through people without forming real bonds, you might just be using dating as entertainment rather than actually looking for a connection.
Signs it's time to trim the roster:
If your roster feels more like a chore than a love life, it's time to narrow it down and focus on quality over quantity.
Casual sex can be amazing. It can also feel like an emotional roller coaster designed by someone who really enjoys watching people suffer. One minute you're both on the same page - "just fun, no feelings" - and the next, one of you is staring at your phone, trying to decode why they left your last message on read for exactly 8 hours and 14 minutes.
The truth? Sex is not casual if you're catching feelings but pretending not to. If you know you can separate emotions from intimacy, great! But if you're secretly hoping that one more hookup will change their mind and make them see you as "relationship material," please save yourself the heartbreak. You deserve someone who wants to be with you because they actually like you - not because they occasionally want company at 1 a.m. (Chapter 18 covers all you need to know about sex and modern dating.)
Dating apps should come with a disclaimer: "Warning: Some people here are not who they claim to be." You match with someone who looks like a Greek god in their photos, and then - boom! - you meet up, and they suddenly look like the "before" picture in a skincare commercial.
And it's not just about looks. Some people catfish with personality. You think you're talking to someone fun and interesting, but then you meet them in person, and they have the charisma of a tax return. If their energy over text is giving "romantic comedy lead" but in real life they're drier than an unsalted cracker, you've just been personality catfished.
Lesson here? Video calls before the first date can save you from unexpected jump scares. Also, if they only have one blurry group photo and won't send a selfie? Run.
Remember when we all collectively forgot how to socialize for two years? Yeah, dating post-pandemic still feels like that. Half of us reentered the dating world with the energy of a puppy finally let outside, while the other half still flinch when someone reaches for a handshake.
Common symptoms of post-pandemic dating anxiety include
The good news? Everyone else is feeling just as weird. Dating is awkward. You'll get through it. Worst case? Blame any social awkwardness on the pandemic and order another drink.
Some people treat dating like it's a reality show - except instead of competing for love, they're just collecting players and seeing who keeps their attention the longest. You know the type:
If you've ever felt like you were on an episode of The Bachelor but with none of the roses, you've probably been played by a heartless romantic. The key to avoiding these people? Look at their actions, not just their words. If someone is stringing you along for fun, they're not your person. Move on before you become just another episode in their highlight reel.
Dating...
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