August 14, 2026 Categories: In Print / Featured / Marriage and Relationships
Timing, Is Everything
Dear Dating Coach,
I have been dating for a few years and last year my parents (with my permission) starting taking suggestions for my younger sister as well. Now she is dating someone very seriously and my entire family believes that an engagement is imminent. My sister is glowing and I am happy for her, but it feels overshadowed by my sadness for myself. I feel like I can’t talk about this to anyone. But I can see how my siblings feel bad for me and how my parents try to shield me from the happy details. I love my sister and I never expected to feel this way. I am sad, and then mad at myself for being sad, and then I feel terrible for being such a horrible sister. I feel ashamed that she will be engaged before me. This process was smooth for her and it has been so difficult for me. I hate that I feel this way. How do I get through this with niceness, and maybe some class and dignity?
Single Sister
Dear Sister,
I was in the airport this week walking to my gate, when I found myself in a full-blown plane-chase. (Yes, this is a made-up term, but I am keeping it.) Flashing lights and blaring sirens filled the airport. (OK, OK, I added the special effects. But I wanted to set the scene. Picture it!) A man ran through the terminal, legs pumping, carry-on flying, as people scrambled to get out of his way. His apology became a mantra (“Sorry! Excuse me! Sorry!”) as he jostled flyers, racing to his gate. I found myself rooting for him as I pictured his morning of late Ubers, unexpected traffic, and faulty alarms. “Go! Go! Go!” I yelled, (quietly, in my head of course) hoping he would make his flight. I saw him check his watch, pictured the hope in his eyes, and saw him skid to a stop at gate 27. “Did I make it?!” I heard him breathlessly ask. Lucy and Lacy (names have been changed, because my eyesight is not that good.) the gatekeepers of 27 (and 28), shook their heads, and everything changed. I saw the energy leave his body, I watched the slump of his shoulders, his head drop, and his luggage topple over, forgotten. He sat in a seat, dejected, as the plane took off, and you could feel his sadness and frustration.
But then, after a while, he stood up, walked to the counter, and Lucy, (or maybe it was Lacy? You choose.) helped him book a later flight. And exhausted from all the drama, I boarded mine.
I Put My Phone on Airplane Mode…
I’m so glad you reached out. Your younger sister is getting engaged. You may have thought conceptually that you would be fine with a hypothetical engagement, but a real engagement has been much harder to swallow. We don’t have to establish that you love your sister and you want to see her happy. We take this as fact. Regardless, the sadness, shame, and anger for feeling this way are eating at you. You worry that you won’t be able to be supportive and generous with your time and heart, and moreover, you worry about how to manage the reactions of those around you as they offer you comfort and even pity.
But It’s Not Flying.
First stop telling yourself not to feel sad, mad, left behind, ashamed, and anything else you find in your feelings’ drawer. This is how you feel. Let’s feel those feelings even though they are uncomfortable. This is not an easy position. It’s hard and so the feelings are hard as well. Be patient with yourself. Be kinder to yourself. Find someone that you trust and share. Vent. Cry. No one thinks less of you as a person, as a sister, or as a dater. Timing is often a mystery. Now it is hers. It’s OK to have expected that it would be your time first.Acknowledging the pain will allow some of it to dissipate. Give yourself permission to be sad for yourself, and also happy for your sister. It’s ok to feel both at once. Hold your head high. Nothing is wrong with you. You will have your time. Then, when you feel ready, you will continue dating, you will continue looking, and you will find the right person for you. You will book a new date and fly toward a lifetime of happiness. We are rooting for you.
