Dating Like a Gentleman: 20 Ways to Show Respect, Kindness, and Class

The other day, one of my sons asked me, “Hey, when’s your anniversary again?” I told him the date, and he lit up. “That’s the same day my girlfriend and I made it official! Do you think that’s a good sign?” He was so earnest and hopeful, and I couldn’t help but laugh at how sweet it was.
While I love his enthusiasm, it also reminded me how important these early stages of a relationship are—not just for making it “official” but for laying the groundwork for kindness, respect, and good old-fashioned thoughtfulness. So, to help my sons—and any other young men out there who want to treat their dates right—I’ve put together a list of tips for dating like a true gentleman. These aren’t just about making a great impression (though they will); they’re about showing respect and being the kind of person someone would be proud to date.
Here’s the playbook. Let’s dive in.

Alright, boys, here's the ultimate guide to being thoughtful, kind, and setting yourself up for success in relationships. Trust Momma, if you follow these, you’ll not only make her smile but also feel good about yourself. Let’s go:

1. Be upfront about the plan. First dates should be simple and mutual. Pick a place together. Surprises are cute later, not now when you don’t know her tastes yet.
2. Be early. If you’re not five minutes early, you’re late. Being on time shows you respect her and value her time.
3. Open doors. Every single one—car doors, restaurant doors, all of them. This isn’t about “old-fashioned manners”; it’s about being thoughtful.
4. Compliment her. Find something you genuinely appreciate—her smile, her outfit, her laugh—and let her know. Authenticity is key.
5. Dress the part. You don’t need to wear a suit, but look like you put effort into your appearance. It speaks volumes.
6. Smell good. A little cologne goes a long way. If she notices your scent hours later, you’re doing it right.
7. No phones. Stay present. Checking your phone says, “I’d rather be somewhere else,” and that’s not the vibe you want.
8. Lead the conversation. Ask her questions, listen, and respond. Show interest in her thoughts, dreams, and what makes her tick.
9. Smile and make eye contact. It makes you approachable and shows you’re paying attention.
10. Make her laugh. Humor is one of the best ways to connect. Don’t try too hard; just be yourself and keep it light.
11. Order an appetizer. Sharing food breaks the ice. It’s an easy way to feel more relaxed and casual.
12. Handle sensitive topics with care. If exes come up, keep it short and mature: “That relationship taught me a lot about what I’m looking for.” It’s about showing growth, not airing grievances.
13. Be honest about your intentions. Whether you’re looking for a relationship or just getting to know someone, be upfront. Kindness is clarity.
14. Pay for the date. Always. It’s not about money; it’s about being generous and thoughtful.
15. Be protective, not overbearing. Walk her to her car, open the door, and follow the “street-side rule.” Show her she’s safe with you.
16. Ask about her world. If she mentions her family, friends, or kids, listen and ask follow-up questions. Being curious about her life shows you’re not self-centered.
17. Express gratitude. At the end of the night, thank her for spending time with you. Thoughtfulness leaves a lasting impression.
18. Be kind to everyone. How you treat the server, valet, or anyone else you encounter reflects who you are. Kindness is never optional.
19. Don’t rush. Respect her boundaries, and don’t pressure her into anything. A great relationship builds on trust and mutual respect.
20. Follow up with care. Text her when you get home to say you had a great time and would love to see her again. Leave her smiling before she sleeps.

Remember, dating is about connection, not perfection. Treat her the way you’d want someone to treat your sister, and always show the best of yourself.

Getting to Know Her World: Thoughtful Questions That Show You Care

​After sharing the importance of showing genuine interest in someone’s life, you might be wondering how to keep the conversation flowing naturally. This is where thoughtful questions come in. Asking the right questions not only shows you’re listening but also makes her feel valued and understood. So, here are some great conversation starters to help you connect and learn more about her world.

Here are some thoughtful, engaging questions you can ask to show genuine interest in her world:
About Family:

1. “What’s the best advice you’ve ever gotten from a family member?”
2. “Do you have any siblings? What’s your favorite memory with them?”
3. “What kind of traditions did your family have growing up?”
4. “Who in your family do you think you’re most like?”
5. “What’s your favorite way to spend time with your family now?”

About Friends:

1. “Who’s your best friend, and how did you meet?”
2. “What’s the funniest thing your friends have ever done together?”
3. “What’s something your friends would say about you if I asked them?”
4. “Do you and your friends have any fun traditions or hobbies you do together?”
5. “What’s the best trip or adventure you’ve ever taken with your friends?”

About Kids (if applicable):

1. “What’s something your kids have done recently that made you laugh?”
2. “What’s your favorite thing about being a mom?”
3. “Do your kids have any hobbies or activities they’re really into?”
4. “What’s something special you and your kids do together?”
5. “What’s the best parenting advice you’ve ever gotten?”

About Her World in General:

1. “What’s something you’re really proud of in your life right now?”
2. “Who inspires you the most, and why?”
3. “What’s something you’ve always wanted to do but haven’t had the chance to yet?”
4. “If you could have dinner with any three people, alive or not, who would you pick?”
5. “What’s a little thing in life that brings you the most joy?”

These questions keep the conversation light yet meaningful, showing her that you’re listening and interested in who she truly is.

Dating is all about connection, respect, and just enough charm to keep her smiling long after the date ends. Follow these tips, and you’ll be on your way to being the kind of guy moms write blog posts about (in a good way).
And remember, boys, if you ever get stuck, just ask yourself: “Would Mom approve?” If the answer is no, it’s probably time to rethink your strategy. Now go out there, smell amazing, and make me proud.
#GentlemanGoals #YouGotThis #MomKnowsBest