- Nice guys can win. It’s sad, but you’ll start to hear and maybe even believe that you need to be ruthless to get ahead in life. You don’t. Remember, women want to feel loved and safe at the end of the day, no matter what their age. You being cruel won’t give them that.
- Be a friend first. As you start dating, my hope for you is that you’ll be her friend long before you’re her boyfriend. You don’t know it yet, but the emotions will be intense and you’ll be ready to dive headlong into the deep end. That’s normal, but try not to rush. Develop a friendship first it will serve you well in marriage someday. The high-intensity emotions of love may burn bright initially, but the flame of friendship in marriage lasts the duration.
- Old-school still works. You’ll hear a million modern ideas about how dating works, but the age-old wisdom of being a man that loves and respects a woman is timeless (and opening a door for her is always classy, no matter how independent she is). It may not be shiny and on trend, but I promise it will win her heart.
- Your heart will break, embrace that feeling.Odds are very good that one of your relationships will end with your heart feeling like it’s been split in two. You’ll have more questions than answers, more regret than jubilation. When this happens, the world will try to show and tell you that you should stuff those broken pieces way down deep. Down where no one can see or hear about them again. It will tell you to move on, move up, move away. But that broken heart won’t get put back together by running from it. Lean directly into it. Cry the ugly tears (no matter what anyone thinks about them), ask the painful questions, and just remember that as cheesy as it sounds I promise you it does get better with time.
- Talk, don’t just text. Technology is great; it’s enabling us to learn more, do more, be more. But there is always a price to pay. Kids your age are communicating far more with texts, snaps and tweets than they are with real life conversations. Be the guy who takes a girl for a Coke and leaves his phone in the car. Or the guy who shuts the laptop and looks her in the eye instead. You’ll stand out quicker than you can imagine.
- Don’t ever honk at her. Perhaps it’s the old-school stuff brewing again, but it won’t go well if I hear you’ve honked from some girl’s driveway as you’re picking her up for a date. Turn your car off, get your butt up to the door, and ask her parents if she’s ready to be picked up. At the end of the night, walk her back to her door and tell her you had a fantastic time.
- Be fascinated with her, not just her looks. Physical looks are great, but buddy, they’re fleeting. And honestly, even if you find the most beautiful girl in the world, there’s always someone prettier. Learn to become fascinated with who she is, how she operates, what she cares about, what her dreams are. They all matter more than her bra size or how many heads she turns at school.
- She’s beautiful, not hot. This probably could have been baked into the point above, but please don’t call your girlfriend “hot.” Especially in front of your friends. Every boy will say they have a hot girlfriend. Tell them she’s beautiful. Better yet, tell her she’s beautiful. Show her she’s more than the way she looks, and you know that.
- Become a great question asker. We all love talking about ourselves, and we feel most connected to the people who really listen to us. Become the kind of guy who asks more questions than gives answers. That listens more than he speaks.
- Show her parents she’s in good hands.Remember that every girl you date is someone else’s daughter. They’ve spent years and years with her, while you’ve probably only known her for a few months. So earn their trust, too. You do that by doing what you say you are going to do, being home on time, and treating her like their daughter, not just your girlfriend.
- Develop other intimacies beyond the physical kind. The physical intimacy will want to take off like a rocket when you really click with someone. Of course there’s a time and a place for that. But don’t base the entirety of your relationship on it. Find ways to deepen emotional, spiritual, intellectual bonds. Do the hard work here so your relationship is standing on a firmer foundation than simply physical attraction.
- Your sisters are good training ground. When you start dating, you’re probably won’t; no, you definitely won’t have all the answers on how to treat a girl, what girls like, and so on. Remember, you have four sisters. That’s four girls t o learn from, understand, fight with, and love. Let them be your sounding boards; your advice givers. And if you’re ever not sure, think about how you would feel if you knew a guy was treating your sisters that way. That’ll be one of your guiding lights, and your marriage will be better someday because of the lessons you’ve learned from your sisters.
- Create memories, don’t just buy stuff. Sure, every girl loves a good gift. Flowers, jewelry, chocolate—the usual suspects. Definitely still do those things from time to time. But a gift given isn’t the same as an experience shared. Be creative and find ways to share memories instead of gift receipts. She’ll remember that time you went on a wild adventure together far more than she’ll remember the Valentine’s Day rose bouquet.
- Leave her better than when you found her. Sounds like lame advice from your old man, I know, but chances are you’re not going to marry the first few girls you date. Maybe not even the first few dozen. But if you know this, don’t trample these girls along the way. Treat them well, do the right things, and when it ends, hopefully you’ve left them in a better place for knowing you.
- Love well and forgive often. I’m sure this list could be a mile long and it would still fall short. We didn’t even touch on the layups like honesty, respect, don’t cheat, and have fun. But in my years of dating and 12+ years of being married to your mom, I have fallen short in many areas. I misplace priorities, show up late, and break promises. But I’ve learned to ask for forgiveness often. And I’ve worked tirelessly at loving her well. It doesn’t always look like it does in the movies, but the real, gritty, deep love is worth far more than you can imagine, son. Fight for that kind of love. And forgive each other when you miss the mark.
You make me proud, young man. I’m excited to watch your dating story unfold.