Dating Advice, aka Love Lessons for My Children

My dating life spanned a whopping 20 years. Not really my preference for it to have bridged an entire generation, but those are the facts. You could make the case that I’d learned a thing or two over the years. Or given the length of it, you could just as easily say I didn’t.

First a little context: I came of age in the mid-80s, a time when the bulk of my peers did their best to postpone adulthood into their late 20s or even their early 30s. Even still, some really great people I know successfully married at a relatively younger age, leaving it to the rest of us to sort maniacally through the pool of remaining available people.

It was fun for a few years, sure. And then it got depressing, fast. Around Year 17, I got used to the idea of being by myself forever. Sure, a companion throughout life would be awesome and having a family was a dream that eluded me, but marrying the wrong guy was not the answer.

Now these many years later, I am married and watching my young kids grow up. They are still at home and not yet in the dating scene, but the oldest is now older than I was when I first fell in love. It seems time for me to collect my thoughts about this subject.

Believe me, I’ve definitely had more than a few facepalm situations with guys over the years but luckily for me I’ve never been a victim of domestic violence. I’ve never been divorced either, nor do I intend to be. But what follows here is not marriage advice. Oh no! I’m not ready to go there yet.

Nope, for now all I’ve got is some dating advice. Maybe it’s a little on the heavy side. Then again, if it was all sunshine and rainbows, it might not have been a 20-year venture! lol So yes, everything I write about below I’ve learned the hard way, and this is what I jotted down over the span of one evening. I’m sure I will add to it over time, too.

To keep things simple, I’ve written it for my daughter but the advice just as easily applies to my sons. And while I often size up a date/boyfriend/love interest, it’s just as easy to flip this advice around and use it to examine one’s own behavior.

tyler-nix-525388-unsplashSo kids? Listen to your mother as follows, in no particular order.

  1. Love, the kind of love that I wish for you, is a verb that transcends all time and place. You will learn this over a significant length of time. It won’t be the first date. It won’t be the 100th. I don’t know when you will discover it, but I hope you do. And when you do, it’s that kind of love that should propel you into marriage.
  2. Love isn’t a 50/50 proposition because nobody knows where the 50 yard line is in the game of life. It moves all the time because your needs and his forever change. Give because you want to. Give because you love him. Give in a way that doesn’t keep score but on the flip side, don’t go broke or be a doormat in the name of love because that’s not love. That’s desperation.
  3. Love most certainly can be a one-way street, and you will find out that’s true when you get your heart broken. It will hurt like hell. But the best kind of love flows like a current between you both. You’ll be able to feel that and will know it’s right.
  4. Learn to love yourself. Very easy to say but perhaps a little harder to do. Nevertheless, know your worth and hold your head high for as long as it takes. I hope it doesn’t take 20 years for you to figure this out on your own but you never know. You may come to doubt yourself over and over again, but don’t think there is something inherently wrong with you. Sure, we all have things to learn and there are ways we can and should grow, and you will. You really don’t need someone else to prove you’re worthy. You simply are. Don’t forget that, ever. You are an amazing, beautiful, wonderful human and you deserve to spend your days with someone just like that in return.
  5. Know what you want out of a date or a relationship. Are you just looking for someone fun or interesting to hang out with on a short-term basis or are you looking for “The One”? Allow this to inform your dating strategy and be up front about your objective with the other person relatively early on. Don’t waste your time with someone who wants the former when you want the latter and don’t feel pressured by someone when it’s vice versa.
  6. Say no as often as you want or need and dump any guy who refuses to respect that the first time you say it.
  7. Figure out what your primary love language is as you will be lonely with someone who doesn’t know how to speak it. If you don’t know what a love language is, read The Five Love Languages by Gary Chapman. It’s a quick but eye-opening read. Understand that some guys simply cannot learn a different love language other than the one they speak. If you care about someone, learn to speak his love language to really connect with him on a deeper level.
  8. Get attuned to a person’s vibration or energy level and recognize whether yours resonates or clashes with it. This applies to friendships too. Notice whether you lift each other up or if your dude routinely makes the mood spiral down. Being blue once in a while is normal but avoid negative energy vampires as if they’re contagious, because they are. It’s futile to think you can fix him.
  9. Frantic guys are often dealing with insecurity and need to keep busy or constantly crack jokes to make you laugh to feel good about themselves. Sure, it can appear admirable or even be fun at first, but over the long haul, it’s exhausting. Again, check your energy level when you’re around this guy.
  10. Dull Dan, not his real name, may be a really nice guy but he lives a ho-hum life that will bore you to tears. If you’re so bored on a date with him that you start eating the candy necklace off another guy’s neck, you might want to take that as a clue he’s not the best guy for you.
  11. You should be able to sit together in comfortable silence for any length of time without it getting weird.
  12. Be bold enough to ask out the best looking person in the room. Don’t worry if he turns out turn out to be gay when you’re not. Maybe you didn’t realize there is a thing called “gay-dar” and you need to turn it on and tune it in. Hopefully the first person you ask out isn’t gay, but if he is, don’t let it knock your confidence levels down a notch or two for a few years.
  13. While we’re on the subject, confidence is a magnet. Project it yourself and seek it out in others. Do not mistake arrogance for confidence. And while we’re at it, giddiness and gushing on your part is understandable when you’re very young but it’s a turnoff when you’re no longer a teen. Compose yourself and keep your dignity intact.
  14. Every once in a while you’ll meet someone who refuses to change his haircut or get rid of his old clothes. He doesn’t see the world changing around him while you do. Move on. He’s not for you.
  15. Dump immediately anyone who insults you. He’ll claim he was just joking but he does it to feel better about himself. It’s not your job to make him feel better about himself.
  16. Breaking up can be hard to do but do it as soon as you know, and do it face to face.
  17. Ever hear the term “failure to launch”? There comes a time in every young adult life to get a job, start earning a living, move out on your own, and generally grow up. Don’t devote so much time helping a lazy boyfriend off the launch pad that you start to neglect what you need to do for yourself.
  18. Trust your gut. It is always, always, always right. You won’t be able to put it into words. You feel it in your gut for a reason.
  19. If you’re ever lucky enough to meet someone with eyes and heart enough to peer into your soul, and he genuinely loves what he sees and vice versa, don’t EVER let him go under any circumstances. You’ve met your soulmate.
  20. If the relationship “looks good on paper” or he meets some basic criteria to be an acceptable mate but you struggle to connect on an intimate, emotional level, let it go. You’re not right for each other. Sure as hell, don’t take three years to figure this out.
  21. Dump whomever doesn’t introduce you to his friends or let you come over to this house within the first month. See his home. See how he lives and with whom. If he doesn’t open up, he’s hiding you or he’s hiding a life – or a wife – he doesn’t want you to know about.
  22. Give a new relationship a three-month trial. If it doesn’t have positive momentum by then, move on and be relentless about it. I don’t care how awesome he may seem. If he can’t figure out how smart, amazing, wonderful, and beautiful you are in three months’ time, he won’t ever figure it out. You want different things. He doesn’t really want YOU.
  23. Dump the possessive, jealous guy who tries to physically control your body or emotionally control your life. He will try to dictate who you are friends with, where you work, what you wear, and where you live. Dump him fast and don’t look back. His insecurities bleed into more than his love life.
  24. Notice whether his secretary at work screens every incoming call from you or if he’s given you his number to dial him directly. You deserve direct access after that trial period, baby.
  25. Pay attention to how your date treats everyone and everything: cashiers, waiters, parents, siblings, friends, children, the elderly, strangers, animals, the environment, property, and possessions (his or others). You want someone who demonstrates consistent kindness and care no matter who or what is the object.
  26. Absolutely talk about sex, religion, money, child-raising, and politics. Every single taboo! He’ll have an opinion on the first thing, for sure. But if he has no opinion on the latter, he may not have a brain, a conscience, or a care in the world. You do. Make sure you’re compatible when it comes to these things. Make sure. Do you want to spend your life going to church alone? Whatever you do, do it together. Do you want to find out years later that greed and “every man for himself” rules his heart? If you believe in God and he thinks it’s hocus pocus, it won’t work out in the long run. And be totally aligned on the subject of whether you will have kids before you jump into marriage. Don’t waste time trying to convince him of your point of view if it’s different. There are compatible men out there. It may take you much longer to find one and you may have to move to find him, but invest in one who is.
  27. Guys who strive for high status come from every kind of background, but they’re not looking for a companion. They’re looking for a trophy. You are worth far more than that.
  28. Pay close attention to weird idiosyncrasies like the fact that he never, ever takes his socks off, constantly slurs his words, shuffles his feet, sprawls and slumps over whenever he sits a chair, doesn’t know how to look someone in the eye and shake their hand upon greeting them, or cannot put his phone down or turn it off, even for a moment. Do you really want to deal with this forever? If it bugs you now, it will bug you always. You can’t fix him. You have to decide whether you can live with it. So if it bugs you now, believe me, you can’t handle living with it.
  29. Understand your own growth game and his. Are you content with life as-is or do you continue to learn and grow at a high pace? Do you like exposure to new places, people, and things? Then you want to be with someone whose growth potential is as high as yours or you may find that you will leave them behind. It’s ok if your growth potential isn’t on hyperdrive, but you want to find someone whose pace matches yours or else you’ll eventually be emotionally, socially, spiritually, or intellectually misaligned.
  30. Dating will introduce you to new things you find you enjoy. However, don’t twist yourself into a knot becoming a brand new person in an effort to be likable. Discover new things and keep doing them because you love it, not because you love him or want him to love you.
  31. Beware the guy who lavishes you with expensive gifts as he thinks you can be bought. He doesn’t care about your soul.
  32. Beware the guy who heaps praise on you, especially early on. He doesn’t know you yet. It’s called flattery, and when he discovers you actually have substance, he’ll go silent and run, because he has none to offer in return.
  33. Beware the guy who gets pissed off when he finds out you make more than he does. He’ll feel threatened and he’ll be pretty angry about it. In reality, he should be happy for you and applaud your success, but if he can’t, he’ll NEVER get over it.
  34. Notice what it takes for him to lose his cool and how bad it gets. You really don’t know a guy until you’ve seen him angry.
  35. When the time is right, go on a trip together. Believe me, you see a whole new side to a person when you’re with them for 24 hours straight. Make sure you enjoy that person because 24 hours is nothing compared to a lifetime.
  36. Honestly ask yourself whether you like his friends. If they all seem like a bunch of jerks, it’s because he fits right in with them when you’re not around. In a similar vein, ask yourself whether you like his family.
  37. If it all starts to go south after three months, dump him. He’s been on his best behavior up until then but he’s reached his limit. His real personality is starting to reveal itself.
  38. Ambition is healthy but there are limits on both ends of the spectrum. What does he want to make of himself? Does he have any goals what is he doing to reach them? Is he willing to sacrifice everything and anything to reach them, including ethics?
  39. Be open-minded about looks, status, education, and age such that you don’t miss the joy of discovering the beauty inherent in all kinds of guys. Be open-minded but know and hold out for whatever really makes your heart sing because the best kind of love fits like a glove.
  40. Avoid the serial playboy. They get their kicks purely from the pursuit. They don’t need a prize. Don’t waste your time or dignity trying to convert them.
  41. Recognize alcoholics and drug addicts and avoid both. Sometimes they are really good at hiding their addiction. You’re not a social worker, unless you ARE a social worker in which case I would tell you to leave work at work.
  42. Avoid at all costs anyone who is overly aggressive, or physically or emotionally abusive. DO NOT GO THERE. You are more precious than he will ever appreciate.
  43. Break up and don’t look back if you fight all of the time. This should be a big, freaking, honking clue!
  44. Don’t waste your youth fixing broken people. Seek to be evenly yoked and help each other soar.
  45. Do not be afraid to go after who you want when you know in your heart it’s the right thing. Don’t be afraid of looking like a fool or disappointing anyone or stepping on someone’s toes. You may get your heart broken big time and you may never fully recover from it but I’m telling you, do not give up your shot at happiness, waiting for the perfect time in the future to tell him how you feel. “If it’s meant to be it will be” is bullshit. Love isn’t just gonna roll before your feet and present itself. You will have to work for it. Sometimes you will have to stick your neck out there and risk it to get what you want. Because if you don’t? You’ll spend years trying to catch lightning in a bottle a second time, only to find it can’t be done. Respect marriage vows but everything else up until then is fair game.
  46. Sexual compatibility is a real thing. Sexual intimacy is absolutely sacred and beautiful. Let love be the foundation of a long-term relationship. Please be a full-fledged adult perfectly capable of taking care of yourself, satisfy yourself first with green lights on all the aforementioned dating advice, and by all means protect yourself, but try before you buy. Wait a really long time before you do because all sales are final. There are no returns.
  47. No matter what: you and he get to choose whether you will be a “we”. Only you know who is right for you. Not me, not your dad, not your friends, not his parents, and certainly not exclusively him. Ideally you choose each other, with no rush. The right love is forever.
  48. Jitters are normal. When in doubt, don’t.
  49. Flowers are nice. So are kisses on the forehead. Then again, I’m a sucker for romance.
  50. Despite what I said earlier, be with someone who makes you laugh with ease and vice versa. Levity helps you get through life together.
  51. It’s not a race, it’s not a contest. It’s ok to call timeout once in a while. You owe loyalty to no one other than yourself until you pledge loyalty to him in marriage.
  52. You’ll know if he’s The One. You won’t have to ask yourself or anyone else for confirmation. You’ll just know.

Love, Mom

Photo credit: Tyler Nix on

Author: silonda

I'm not your average Midwestern American woman: an older mom to three kids and married to a musician, hiding out in a small town. I’ve worked as a serious business professional my entire adult life but my soul is really an artist. Wonderlust (i.e., insatiable curiosity) and wanderlust lead me to read voraciously and travel often. The introvert in me likes to quietly observe and share what I discover through writing but buried inside is a pretty funny chick full of spunk and verve who is eager to come out and play. Deep thinking and feeling (all the feels) is my default mode and then I'll crack a joke about it. I’m constantly striving to cultivate whatever makes for beautiful and to love UP.

One thought on “Dating Advice, aka Love Lessons for My Children”

  1. On the flip side of number 21 I always told my kids starting in HS that if you do not feel comfortable and mature enough to introduce the person you are dating to your parents then 1 you shouldn’t be dating you’re not ready and two if your uncomfortable doing so then intuitively you know there is something not right about the relationship.

    Now that my kids are young adults they both told me that looking back I was right about that when I told them.

    You did a great job on the list. Lots of great insights!

    Liked by 1 person

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