When I was in high school I remember doing whatever I could to get my boyfriend’s mother to like me. I tried everything. But despite my always cheerful and ever valiant attempts she always remained, I’ll say, cool towards me. When I finally reached the brink of my adolescent insecurities I unloaded on my beau with a frustrated, what the hell?

He just shrugged. “She likes you,” he offered lamely, “but she knows it’s not like we’re gonna get married or anything.”

Um, say what? You can imagine: at seventeen, that stung. She knew. Heck, deep down we both probably knew, too. But she put it out there and there it stayed. And I’ve never forgotten.

I can’t be certain, but maybe because of my early experience, I’ve grown into a mom lacking enthusiasm for adolescent romance. For me, it’s always been a great source of curiosity when anyone else did.

Like my sister, for instance. I’ve forever marveled at her unaffected exuberance of really, truly basking in teenage love. She’d fawn over her kids’ boyfriends and girlfriends, buy them super nice presents at Christmas, happily accept their friend requests and exude genuine excitement over anything about them. Every high school relationship was treated as The One and it was utterly fascinating to me. Consequently (and alas, one by one), every high school break-up consumed her with incredible sadness — for a really long time. It all seemed crazy to me.

I guess I never bought into the hype because well, adolescence is (pick one) silly, volatile, melodramatic and (most of all) fickle. Let’s be real. Is there a more ridiculous time in any life cycle? When my daughter was in middle school (before it was the norm for third graders to carry cell phones) a young boy called our house and left a very detailed message on our home answering machine asking her to go on a date to the movies. I listened to it, rolled my eyes towards the heavens, promptly deleted it and told my daughter about it – many, many years later at the Thanksgiving dinner table. Why? Because it made for a great family laugh and — like Carrie Bradshaw being broken up via Post-it note — there are some dating behaviors that are beyond reproach. Rest assured: no daughter of mine was ever going to the movies with any kid without a clue.

That was all well and good (and, okay, somewhat controllable) in middle school, but it seems before I could throw in another load of laundry – and despite my inclination to ignore them — I’ve acquired a slew of significant others in my life. And it’s become harder to remain, I’ll say, cool towards them.

My eldest son, a young adult so unsharing of information I couldn’t tell you his favorite color, suddenly started showing up with a stunning girlfriend. Turns out they’ve been together for months. She is well-spoken and personable and bright and — dayum! — pre-med. She possesses such exceptional attributes it is impossible not to enjoy her. She’s a darling. Dang.

My high school senior has been with his girlfriend for quite some time, too. As much as I tried to remain aloof and indifferent towards them, her ability to get him to do homework and come in before his curfew has broken down my tough demeanor. She is an absolute delight to be around and I completely adore them together so of course it worries me. Again, 17. Double dang.

My youngest, teetering on 16, might trouble me the most. He’s been spending his time with such a sweet and charming young lady I find myself lamenting, this – they — would be perfect …. in about ten years….

Good grief, what is happening here? Of late I’ve been wondering which is worse: that these kids’ impeccable choices are turning me soft, or that maybe my sister was onto something.

It’s a tough seat to sit in for sure. And because moms were once teenagers too, we know with assured wisdom that as much as young love blossoms with ferocity, it will also (more often than not) fade with some sadness. Being invested in our kids’ relationships carries weighty fallout when a happily ever after doesn’t happen.

My little girl, now an extraordinary and beautiful young woman, is experiencing her first real break-up and – I have to be honest – my whole family is feeling the strain of her sorrow. (Truth: her grace and reflection while deep within heartache far surpasses her mother’s 1980s coping method of Diet Coke and cigarettes. Geeze. I thank God those DNA strands didn’t swim too strongly.)

We liked him. We Sally-Field-really-REALLY liked him. They shared a lengthy time together and we were all a part of it in some small way. But it just wasn’t meant to be. So now we’re all sad.

And my heart is hurting having to watch her go through this tough time.

I knew I shouldn’t have gotten him that bathrobe for Christmas.

I should’ve known better than to think my sister was smarter than me.

Tina Drakakis blogs at Eyerollingmom and recently was featured in Huff Post. She appeared in the Boston production of “Listen to Your Mother: Giving Motherhood a Microphone.” Her work has been featured in NPR’s “This I Believe” radio series yet she places “Most Popular 1984” on top of her list of achievements. (Next would be the home improvement reality TV show of 2003 but her kids won’t let her talk about that anymore). A witty mother of four, she takes on cyberspace as @Eyerollingmom on Twitter and Eyerollingmom on Facebook & @Eyerollingmom on Instagram. Her collection of essays, A Momoir, can be found here