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This is my little boyfriend. He is five. I love him more than life.

Someday, he will become one very lucky girl’s Prince Charming. As much as I want that lucky girl to be the perfect girl for him, I also want him to be prepared for her.

I recently stumbled across this love note from Sara to her young son. I begged for her to come guest post as it is simply the best advice a mother could ever give her son concerning dating. It’s everything in my heart, magically put perfectly into words. Sara, thank you for sharing this sweet advice with us.

—

Dear Son,

Dating is a tricky thing and doing it right is difficult. But it is honestly, the most important thing you will ever do. Because how you date will dictate who you date. And who you date will become your wife. And who your wife is will determine your future family and so forth and so on. So date wisely.

Here are a few expectations I have for you when it comes to dating:

1. Always ask a girl on a date. Straight forward & direct. AND always ask in person. If that just isn’t possible then ask over the phone. Never, I mean never, ask a girl on a date through a text, instant message, or email.

2. Always take a girl out on a date. None of this “let’s hang out at my place & watch a movie” nonsense. I expect you to pick her up & take her somewhere. It doesn’t have to be fancy or elaborate or immensely creative. Sometimes the best dates are simple, like a picnic in the park. You should always make sure you take her to a place you know she will feel comfortable & enjoy.

3. Open the car door for your date. Open all doors for your date.

4. Pay for your date. No questions asked. Your father & I will make sure you always have money for your dates. Do not ever split the bill.

5. Walk to the door to pick up your date. Never text from the car, or worse yet, HONK! And always walk your date to the door at the end of the night.

6. Use your good senses when it comes to kissing. Don’t kiss every girl, but don’t be afraid to kiss the right girl.

7. Listen to your date. The best dates involve getting to know the other person so take your date somewhere that will allow you to talk. Ask her questions & share insight about yourself. The purpose of dating is to find someone you could spend your future with. So the longer you date a person, the more you should get to know her.

8. Always make your intentions clear. If you aren’t clicking with a girl then end it. Don’t string her along. It may hurt her for a minute but she will appreciate your honesty. And if you are feeling a connection then let her know. A girl loves clarity. It will make the whole dating process easier if you follow this one simple rule.

9. Date around, but only seriously date one girl at a time. Once you’ve found a girl you are interested in and going exclusive with, be faithful to her. Always, always be faithful. If you decide things aren’t working out or you meet someone else you’d like to get to know, refer back to rule #8.

10. Be physical. The right way! Hold hands, put your arm around her shoulders or eventually her waist, kiss her head, put your hand on her knee, these sweet gestures speak volumes & make a woman feel cared for. Going too far physically only confuses the relationship & it can never be undone.

11. Handle her heart with care. Women are strong, but they are also delicate. Don’t ruin that. Do not be responsible for hardening a woman’s heart.

12. Get to know her family & friends and let your family & friends get to know her. Especially Me.

13. When the time comes, tell her you love her, a lot. In fact, tell her all sorts of nice things. Everyone deserves to be complimented.

14. Serve her. Not like a waiter. Perform acts of service for her; make her breakfast, take out her trash, offer her your jacket when she’s cold, you get the point.

15. Surprise her. Again, a little can go a long way. Just stick with small surprises. Bring her a case of her favorite soda, pick her flowers, or show up at her work for a surprise lunch date.

16. Never underestimate the power of the written word. As nice as it is to hear good things, it’s even better to have them written down so you can reference back to them. You should write letters or notes to your love often.

17. When the time is right & you’ve found that special someone, get down on one knee & ask her those 4 special words.

I love you now, forever and always. And know that someday, I’ll love her too.

Love, Mom

—

Sara started taking her boys on official dates once they hit the age of five. They have a whole lot of fun making memories, but the whole purpose is to teach them how to date.



*Stop by Sara’s blog Team Watkins for more great reads about life, love, and motherhood in Hawaii.

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