A Dad’s Letter to his Daughter About Dating in The Modern World

My incredibly loving & restless daughter,

It’s nearly midnight, and you woke up crying for me just as I finished cleaning up the trail of stickers you somehow managed to place on every surface in the house. You’re finally back to sleep, clutching your Bluey doll in one arm, and my hand in the other. At two and a half, your biggest concerns are whether we’ll read “just one more” book before bedtime and if tomorrow we’ll spend all morning drawing, playing play-doh, doing puzzles, and listening to the shaky egg song on repeat.

But as I sit here with you now, watching your peaceful breathing, I can’t help but think about the choices that lie ahead of you. While you’re dreaming of finding seashells and eating ice cream cones, I’m writing this guide about one of life’s most consequential decisions: choosing a life partner. Sure, it might seem premature to write dating advice for a toddler, but in roughly fifteen years, you’ll be entering the most opportune time to find love – your college years. And in this rapidly evolving world of dating apps, shifting social dynamics, and changing expectations, I want to share some timeless wisdom that I hope will serve as your compass when your heart starts leading you into uncharted territories while I still remember what those days were like myself.

Consider this letter a field guide to modern love, written by someone who’s navigated, and watched many others navigate these waters and wants to help you avoid the hidden reefs and dangerous currents. From the organic opportunities of college dating to the complex world of dating apps, I’ll share some raw insights that I hope will help you make choices that lead to lasting happiness and contentment.

The College years: Love’s Organic Market

Try to capitalize on the easiest period of your life to find a partner. Unlike post-college life, where dating often relies on apps or organized events, college provides countless everyday interactions. From classes to parties, college life is filled with opportunities to meet people organically. After your college years it becomes more and more challenging as those organic opportunities with people in your peer group start to dissipate with age, increased responsibilities, and an ever depleting dating pool.

However, don’t force it. If no one’s ticking your boxes, or a relationship falls through, know that it’s ok. Love can be found at any stage of life, and often finds you when you least expect it.

Pro Tip: Be mindful of the guy’s choice of major. If he dove in to a $200k debt commitment and didn’t consider or care about his choice of major’s earning potential that’s a big red flag. That care free gender studies major might be appealing now while everyone’s living in dorm rooms and eating cup of noodles and grilled cheese sandwiches, but you probably won’t be as cool with that standard of living in your 30’s & 40’s while you’re paying off his student loans.

The Profile Puzzle

These days, picking a date is like shopping in a human catalog. You’re swiping based on abs and stats more than ever, because let’s face it – personality, humor, kindness, and brains aren’t exactly jumping off those dating profiles. It’s a looks-first world out there, but don’t let it fool you.

Don’t Let Instincts Drive the Wheel

Here’s something crucial: don’t let instinctual primal desires be the main driver in selecting a mate. That tall, muscle-bound, tatted up guy might make your heart race, but remember – we’re not living in the Stone Age anymore. Those physical traits that once meant survival when we were fighting off predators and rival tribes? They don’t provide the same benefits to you and your potential offspring in today’s world.

That is unless of course AI has gone haywire and we’re suddenly in an apocalyptic society (in which case, please disregard this entire letter), otherwise you need more than brawn to build a happy life together. Look for the qualities that matter in our world – emotional intelligence, problem-solving skills, and the ability to navigate a Costco on a Saturday without losing his cool.

Arbitrage in the Dating Market

Now, let’s talk strategy. As with everything in life, be on the lookout for arbitrage opportunities. The current dating market is overvaluing male height, flashy cars, chiseled jawlines, perfectly quaffed hair and piercing blue eyes like they’re the next Bitcoin. So, consider placing a higher level of importance on other attributes that reveal the person’s true character. Do the cost-benefit analysis. That tall dude, with the piercing blue eyes, flashy car and perfectly quaffed hair? He’s overvalued, and this will have a trickle-down effect on his behavior and expectations.

Don’t get me wrong, I’m not saying you should be looking for a mixture of Quasimodo, Mother Teresa, and Warren Buffet. The point is you’ll be better suited seeking out the things that truly matter in your partner than prioritizing overvalued superficial assets. Instead, look for the undervalued assets. Maybe it’s the kind hearted, good looking average-height guy with a wicked sense of humor and a stable job. Or the charismatic, shorter guy who’s killing it in his career or business and treats you like a queen. Remember, in the long run, you’ll get more bang for your buck with qualities like kindness, ambition, and emotional intelligence then inherited traits, or that car Grayson went into debt to impress ladies with less finely tuned bull shit detectors than yourself with.

The Goldilocks Zone of Self-Security

No matter who you choose, make sure they’re secure in themselves – but not so much that they’ve crossed over into narcissism territory. You want someone confident enough to support your dreams without feeling threatened, but not so full of themselves that they can’t see past their own reflection.

Watch out for jealousy – it’s a relationship killer. A little bit might seem flattering at first, but trust me, it can get ugly fast and destroy even the strongest relationships. You want a partner who’s secure enough to celebrate your successes, not someone who sees them as a threat.

Make Sure You’re Fishing in the Right Pond

Listen up, because this is important: understand your league, especially as a female in today’s dating scene. There are plenty of grade A D-bags out there who’d be happy to take advantage of you. It’s your job to sift them out.

I know you’re a catch, but if you’re constantly chasing after the hottest guy in every room, you might end up with nothing but a string of casual encounters and ghosting stories. That six-pack and chiseled jawline come with a price tag you might not want to pay.

Character: The Non-Negotiable

Never, ever settle when it comes to character. I don’t care if he looks like he just stepped off a movie set – if he’s not kind, respectful, and treating you right, show him the door. You can adjust your expectations on looks, but not on how someone treats you. If all the guys you’re dating turn out to be a-holes who try to use you and then disappear, it’s time to recalibrate your choices.

Ambition and Work Ethic Matter

Here’s the thing – he doesn’t have to be the CEO of a Fortune 500 company, but make sure he’s got a good work ethic and a desire to always better himself. If he’s spending more time playing the latest video game or watching sports than pursuing meaningful passions, and self educating he might not be the one. Look for someone who’s driven to grow, learn, and improve. That ambition will serve you both well in the long run.

Financial Stability is Key

While we’re on the subject, keep an eye out for someone who can support you and your future family with the kind of life you’re hoping for. I’m not saying he needs to be rolling in dough, but he should have a plan and the motivation to provide stability. You want a partner, not a project.

The Long Game

Remember, you’re not just picking a partner for yourself, but potentially the father of your future kids. So ask yourself: Is he conceited and narcissistic, or kind and loving? Does he show compassion for others? Is he good with animals and kind to the waitstaff? Is he working towards goals or just coasting? If he’s ticking these boxes, you might have a winner. Make your choice based on who makes you happy now and who’s likely to keep you happy (and stable) in the long run.

Dodging the Duds

If you follow this advice, you’re less likely to end up with a deadbeat, abusive, or cheating loser. But even if you find your Prince Charming, remember that life isn’t always a fairy tale. There will be tough times, so be resilient in your love for each other. Don’t scapegoat each other when stress hits – work through it together.

Keeping the Spark Alive

Here’s a big one: don’t mistake the lack of that initial spark for a lack of love. When that new relationship buzz wears off, don’t go chasing it with some flirty guy at work or the gym just because he’s making you feel good about yourself. That infatuation period is fun, but it won’t last with any Liam, Logan, or Wyatt and before long you’d be right back in the same place as you were with the last guy. The infatuation period may fade, but real love grows deeper over time.

Kids Change Everything

When you bring a child into this world, you’re molding the next generation. Your partner will play a huge role in shaping their values, character, and overall outlook on life. Is he the kind of man who will model respect, integrity, and compassion? Will he teach them to treat others with kindness and to stand up for what’s right? Can he provide a stable and loving environment where your children can thrive?

Beyond that, think about the support system you will have in place. Parenting is a challenging journey, and you need a partner who will be there through the sleepless nights, the toddler tantrums, and the teenage angst. You want someone who will share the responsibilities and joys of raising children, who will be your ally and your rock.

Final Dad Wisdom

The person you choose as a partner will not only impact your life but also the lives of your future children. Choose wisely, and ensure they are someone who will be a positive influence and a steadfast presence in your children’s lives. Children need their father, and the sad truth is, the number one predictor of child abuse is a stepparent in the house, surpassing even an alcoholic biological parent by more than 100 times the risk. So be careful not to prioritize your choice with who boosts your status the most amongst your peers in your late teens and 20s and instead opt for someone more likely to be reliable for the long haul.

You’re perfect to me, even if you don’t end up dodging some of my less than stellar traits. If you’re to find that you need to make a couple of sacrifices in the dating pool to live your best life, just make sure you’re not sacrificing the things that truly matter.

Remember, as long as you find someone who loves you even a fraction as much as I do (which is still a whole lot), you’ll be okay. Just don’t do like your mom did and settle in every conceivable way. You deserve better than that.

Be careful out there. The dating world can be tough, but you’re tougher. And remember, no matter what, you’ve always got me – your slightly overprotective, always loving dad.

Love, Your Old Man​​​​​​​​​​​​​​​​

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