Helping a Brother Out

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Helping a Brother Out

Yesterday, my baby brother (and only sibling) Drew married the love of his life in a beautiful sunset ceremony overlooking the Hudson River. To say that it was one of the most meaningful, significant weekends of my life would be an understatement. My family has always been close – in fact, my brother and I lived together his first four years here in NYC.  I thought living together was a beautiful bonding experience. He thought it was a living nightmare. In any case, he still trusted me to give the closing speech at the reception last night. I was truly overcome looking out into the crowd to see my handsome, beaming baby bro, his beautiful bride, and our family and friends from both near and far (Brazil!) to be here. I was so excited to share some special stories with everyone there, and I also wanted to share them with YOU!

Through my work helping people find love, I’ve found that I have as much to learn from the relationship of others as I do from my own experiences. (Believe me, being the Jewish, unmarried, older sister, I’m sure I should probably personally follow the lessons I’ve learned from couples like my brother and his wife more than I have!) In any case, as a dating (read: NOT relationship) expert, I do like to think I played a pivotal role in helping my bro land this beautiful woman that he can now call his wife. 

Those of you who have known Drew and I throughout our lives know that puberty was particularly cruel to the both of us and lasted into young adulthood. In fact, when my brother came to join me in NYC 5 years ago, his only real experience with girls was with Cortana on Halo XBox Live. He met Dani in NYC pretty quickly, but he was definitely secretive with me about it. I knew something was going on, though, when he invited a real live girl to our New Year’s Eve party. Soon after, he told me he took her out on a first date and had an amazing time.

“So,” I said to him. “Will there be a second date, I hope?”

“Well, she actually got pretty sick,” he told me. “I know I like for people to leave me alone when I’m sick, so I guess I’ll just hear from her when she’s better and wants to go out again. Oh, and it’s also her birthday, and I don’t want to bother her.”

Um… no way, Drewie.

We had a little chat. After my brother shared with me that she had told him her favorite food was a very particular kind of pasta, I told him, “Go to Eataly and find that pasta, and then stop by the deli to pick up some good matzoh ball soup. Put it in a bag with a note that says, ‘Happy Birthday! Hope you feel better soon’ and drop it off with her doorman. Don’t tell her, don’t see her – just do it.”

That delivery marked the beginning of not just a special relationship between my brother and his now-wife, but also between him and her doorman! I really wish my ex had had an older sister who had advised him not to bring me 16 Handles frozen yogurt after my wisdom tooth surgery he had forgotten about, saying, “Damn, you owe me $8  – the gummy bear topping was way too expensive.” (Really, what guy who knew me would get me gummy bears as a topping? And frozen yogurt that wasn’t even sugar-free! AND after wisdom tooth surgery? He was actually an orthodontist. No joke.)

Really, though, my own failed experiences helped me pave the way for my brother, and they also helped me live vicariously through him, especially when it came to helping him plan his first anniversary with Dani.

Drew asked what he should get her for this milestone in their relationship. Learning from my own previous relationship in which I received a pair of socks and Under Armour leggings (which didn’t even match), I told Drew to go to Tiffany and get Dani a beautiful, simple, sterling silver Tiffany-heart bracelet. He asked me to come with him as his only experience with jewelry was being dragged into Chico’s with my mom at the mall in Georgia. We couldn’t coordinate a time to go, so he ended up having to go on his own, with me “on call”.

“Ok, I‘m going in,” he texted me. Then, just two minutes later, my phone rang: “Forget this, sister! I’m outta here. They don’t have it. Whatever.”

I was confused. “Wait, Drew… what happened?”

“Well,” he began. “I went in and asked ‘So, where are your stainless steel bracelets?’ and they gave me a look and told me they don’t carry that.”

“Of course they don’t, Drewie,” I said. “This is Tiffany, not a medical alert supply store in The Villages (our parents’ retirement community in Florida)! Go back in there and ask where the sterling silver bracelets are.”

Ten minutes later, he texted me that he was good to go, turquoise Tiffany box in hand! I then suggested that he give her the bracelet when he takes her to the most romantic restaurant in the city, One if by Land, Two if by Sea –  not a vegan dinner with his mother where my other ex took me on our first anniversary. Yes, living vicariously through my brother has been awesome!

In any case, while I like to think I helped my baby brother Drewie get through some crucial early milestones in his relationship, it’s really been amazing to watch them both grow together as they’ve fallen so deeply in love. I’m so glad that my amazing, hardworking, thoughtful baby brother – a young man who is genuinely good to the core – found his beshert. I do, however, wish her luck with putting up with his compulsive nail clipping habit, his setting off the fire alarm every single night when he cooks sweet potatoes, and his overly long convos with doormen and customer service reps (shout out to Ray, Felix, and every Delta agent in the world!).

As this Jewish year comes to a close, I hope we can all take a moment to cherish the loving relationships we have in our lives, and to be supportive of all of the wonderful relationships around us. May we continue to learn from our own experiences as well as others’. Thank you to my brother, for adding so much to my life. Wishing Drew, his new wife, and all of you love, health, and happiness in 5778 and in every year to follow!

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