Wedding Wednesday: We are Engaged!!

Wedding Wednesday Series :: Post 1 :: Our Engagement Story :: Effortlessly With Roxy
Many happy days ahead. Kicking off Wedding Wednesday: We are Engaged!
Photos taken April 2017 in the Brooklyn Botanic Gardens & on the Brooklyn Bridge

It’s the news I’ve been celebrating for over a year now: I’m engaged to be married!! About 90 days from now I’ll be the luckiest girl marrying an amazing guy on what will hopefully be a sunny day right here in NYC.

I know how fun it is to plan a wedding, attend a wedding or even just talk about weddings! That’s why today marks the launch of my Wedding Wednesday series. I’m very excited to share many of the details and goings on of Alex’s and my engaged experience.

As one of the last people in my group of friends to walk down the aisle, we’ve had immense help and guidance in planning our wedding. Yet even with that help there is so much I’m learning along the way. I want to bring you along for the ride as we prepare to walk down the aisle!

Originally I’d planned to start this series over the Winter. However, we chose to have a long engagement (more about why in an upcoming post) so for a long stretch there really wasn’t much to talk about. In fact things didn’t really kick into high gear for us until a couple of months ago. It’s only in these last 3-4 months before our wedding that I understand why brides can be so stressed out!!

But we’ll get to all of that. For now, let’s talk about one of my favorite stories: how Alexander and I got engaged.

Wedding Wednesday Series :: Post 1 :: Our Engagement Story :: Effortlessly With Roxy
All photography in this post by Laurel Creative, our official wedding photographer.
I highly recommend Lauren for engagement photos, wedding photos, or baby shoots!
Visit the Laurel Creative: website | facebook page | instagram

If you’ve been reading this blog for a number of years you may know that I was previously engaged in 2010 at age 28. And actually, I was engaged once before that in high school too. In both of those cases, I felt far too young to be walking down the aisle. I felt like my life was still in development and I was unsure of what I wanted or needed. I ended up breaking my high school boyfriend’s heart, something I still feel guilty over to this day. My later breakup was more amicable.

Marriage was something I started wanting around age 32. But truth be told, I don’t think I was really ready to be a wife until around 35 or so. (I’m 37 now.) Perhaps being ready isn’t something that’s required for a marriage to successful. But in the last 5-6 years I’ve done so much emotional repair work and emotional growth. My capacity for love and compassion has grown in leaps and bounds. My ability to not be selfish has increased exponentially. I’m not saying that I am perfect now or done growing — only that I feel ready to undertake the commitments that being a wife brings.

Wedding Wednesday Series :: Post 1 :: Our Engagement Story :: Effortlessly With Roxy
My engagement ring is a sapphire surrounded by diamonds on a rose gold band.
It was made by a jeweler in Manhattan’s Diamond District recommended by a family friend.

The most solid argument I have for marrying Alex is that our relationship has always flowed easily. It’s been the easiest relationship either of us have ever been in. Yes, we fight. All healthy couples do! But we hardly ever yell and there is always an underlying partnership and commitment to understanding each other even while arguing.

We met in the Fall of 2015 on a dating app. Our first date started as a simple meet up for a drink after work at the now-closed (*cries*) Flatiron Lounge in Manhattan. Alex picked a spot that was convenient for me — that was the first tick in his favor. Drinks went well enough that it turned into sushi dinner, which turned into Alex sending me home in an Uber.

He was always steady about planning the next date right after the previous one. Although I was seeing several suitors at the time, Alex stood out as being consistent and forthcoming in his interest. I knew things were growing in a good direction when we spent New Year’s Eve of 2015 together. It was an amazing night capped by watching midnight fireworks in Prospect Park (Brooklyn). That night was also the first time Alex said “I love you.”

We took our first vacation together in February of 2016 and by the end of the year we were moving in together. I moved allll the way to Brooklyn. It seemed like a huge sacrifice, but then again Alex made the even bigger choice to sell his apartment (which he felt was not big enough for us plus his two cats and my dog) so we could find a new place together.

Wedding Wednesday Series :: Post 1 :: Our Engagement Story :: Effortlessly With Roxy

At first, living together was a huge adjustment. It was a rocky period for sure as we got used to each other’s routines, animals and decor styles. This period was the most we’ve ever argued. I’m so glad we moved in together before getting engaged, because a ring might have been one bit of pressure too much.

Over time however things steadied. By the Summer of 2017 my friends and family were starting to ask if we had plans to get engaged. Oh how the ones we love can plant those seeds! I started to wonder too and had hopes that our 2nd anniversary might be the right time. Yet when October came Alex instead said he wasn’t ready, which had me wondering whether he was the right guy for me to be with forever or not.

Unbeknowst to me, shortly after our two year anniversary in October of 2017 he started floating the idea of us getting engaged. He asked friends and family about their perspectives on married life. Alex started thinking about rings and told his Mom he was thinking of asking me.

My closest friends counseled patience and I’m so glad they did. When November rolled around and it was time to make our Christmas lists, my friends suggested putting an engagement ring on the list. So I did! I linked to three styles I liked.

I had no idea but Alex had already started working with a jeweler on a ring for me — and had to completely change design course when he saw what I wanted! He also used my wishlist as an opportunity to get important details.

Wedding Wednesday Series :: Post 1 :: Our Engagement Story :: Effortlessly With Roxy
That Alex, such a sly guy!

I couldn’t help but share the screenshot with my girlfriends. The excitement reached a fever pitch! They were happy for me. I was happy for me and Alex!! But suddenly the wait for the ring became excruciating. Looking back on it I fell into the trap of being impatient.

While some of my patient girlfriends counseled me to wait, others were texting me practically every day guessing when the ring might come. “I’m sure it will be today!” said several girlfriends on Thanksgiving. (It wasn’t.) “Tonight would be perfect,” two friends said on the first night of Hanukkah, followed by “It has to be tonight!” on the last night. It wasn’t then either.

By Christmas, my excitement over the possibilities was turning into frustration. I didn’t know until later that Alex had the ring and was just waiting for the right time. Knowing my love of fireworks, he was thinking New Year’s Eve would be perfect.

Wedding Wednesday Series :: Post 1 :: Our Engagement Story :: Effortlessly With Roxy

But he quickly changed his mind! We spent Christmas with his family in Sag Harbor NY as is our tradition. His parents, aunt and uncle and cousin and her boyfriend were all there. On Christmas day we each take a turn opening a gift. My last gift just so happened to be a box. A ring-sized box. A ring-sized box from Alex!!!

This is it for sure!! I thought to myself. I opened the gift slowly, wanting to savor every moment. Everyone was watching me as a smile spread across my face. But when I opened the box, it wasn’t a ring. I can’t even remember what it was anymore; I’m sure it was lovely but it wasn’t an engagement ring and I couldn’t hide my disappointment.

Between the right-sized box but no ring and my phone constantly lighting up with “did he ask yet?” texts, I was crestfallen. I sadly texted back “no” to all my girls. By dinner I was nearly distraught. Alex saw my sadness and made a new game plan.

After dinner, we all opened holiday crackers. You know, those party favors that look like giant candy wrappers with twisted ends. When you crack them open inside there is a paper crown, a mini toy of some kind and a riddle. We went around the able asking each other riddles.

Alex went last. When it was his turn, he said, “I have something to ask Thea.” (That’d be me, y’all know by now that Roxy is a nickname, right?)

Before I knew what was happening, Alex stood up, walked around the round table to where I was sitting, got down on one knee and asked if I would marry him!! And I of course started bawling because up until that very moment I’d been so very sad but just like that I switched to elation!! Everyone started cheering and I just kept crying.

Wedding Wednesday Series :: Post 1 :: Our Engagement Story :: Effortlessly With Roxy

I’m so grateful that Alex’s cousin Lily got her camera out and snapped a few photos!! It’s a moment I will never ever forget. We excused ourselves for a few minutes to call my Mom and Sister, and then came back upstairs to celebrate with Alex’s family for the rest of a wonderful night. A few months later in April we took our engagement photos while the magnolias were in bloom, with the cherry blossoms about to open.

When others have asked Alex why he decided to propose or when he knew he wanted to marry me, he doesn’t have one solid answer. (Or more likely knowing his personality, he doesn’t want to share.) When our officiant asked us during our initial meeting with her, Alex said my happiness is important to him and he knew getting married would make me happy. Pardon me while I melt into a puddle on the floor over here!

It’s funny. We got engaged on December 25, 2017. In the time since then we’ve had friends who have gotten engaged and married (we’re attending just such a wedding this Friday!!). In this time Alex’s brother reconnected with an old flame, they got pregnant and married and now have a 4-month-old baby!! Alex’s Mom and Dad are basically having the best 18 months ever. Several of our friends have gotten pregnant, to the point that my girlfriends now say Alex and I getting engaged is good for fertility.

Wedding Wednesday Series :: Post 1 :: Our Engagement Story :: Effortlessly With Roxy

It’s amazing how our long engagement has allowed so much happiness to develop around us. And for us, it’s allowed us to enjoy this very temporary time. I love being called ‘my fiancée’ by Alex! I love calling him my fiancé! (He doesn’t like the word very much, but then again most guys don’t.)

I adore the feelings that come with the knowing anticipation of a wedding. I like all the questions about how we met, when we knew, what we’ll do and so on. I’m enjoying the countdown to becoming Mrs. Alexander Cripps.

And in another way, as much as this day is about us, I’m also enjoying all the happiness this time brings forth inside of me. It’s hard not to be happy when you know that a wedding is on the horizon with all its happy moments to come.

As this Wedding Wednesday series you can expect the story of my experience planning our wedding. I’ll share resources I’ve used and helpful sites I’ve found. Plus I’ll be sharing how to plan a great engagement party and bachelorette weekend! There will be reflections, lessons I’ve learned and more. This series will continue to run after our actual wedding so I can share how everything went too.

If you are (or were) married, how did you get engaged? Was it a surprise or planned? Who was the first person you told???

Thank you to the following sponsors for their support of Effortlessly With Roxy, 
Wedding Wednesday and my upcoming wedding to Alex!!


Kleinfeld (Wedding Dress) || RenzRags (Bridesmaid Dresses) || Amazon Fashion (Accessories) ||
Basic Invite (Save the Dates) || Laurel Creative Photography (Engagement + Wedding Photography) ||
Mango Tree Productions (Wedding Videography) || Love & Promise Jewelers (Wedding Rings)
Hyatt House Jersey City (Wedding Hotel + Afterparty) || VistaPrint (Mailing Labels)
Jewel by Badgely Mischka (Wedding Shoes)



  1. May 15, 2019 / 1:22 pm

    Oh my goodness congrats!! Loved reading your story and that ring is just beautiful!!

    • May 16, 2019 / 4:47 pm

      Thank you Hillary! Alex did an amazing job with my ring, the blue is like his eyes and I can't help but smile every time I look at it!

  2. amles
    May 15, 2019 / 2:25 pm

    I adore a good love story! Thanks for sharing. You are both glowing with happiness. Best wishes and congratulations to you and your beau! xoxo

    • May 16, 2019 / 4:47 pm

      Thank you amles!! 🙂

  3. legalleeblondeblog
    May 15, 2019 / 3:25 pm

    What a sweet engagement story and I absolutely love your unique ring!

    • May 16, 2019 / 4:47 pm

      I'm so glad you enjoyed it!!

  4. rainbowflash94yahoocom
    May 15, 2019 / 5:39 pm

    Oh I just loved reading your engagement story, Thea! What a special story- and how cool you two met online! 🙂 Enjoy the last few months as a fiance!

    • May 16, 2019 / 4:48 pm

      Thank you! Yes isn't it crazy that we met online? Although that's becoming so much more normal now — we've gone to 4 or 5 weddings in the last 3 years for couples that met online.

  5. Marilyn Palmer
    May 15, 2019 / 6:18 pm

    congrats, Roxy and Alex! so happy for you two! Been following your blog for years!

    • May 16, 2019 / 4:49 pm

      Thank you very much Marilyn!!! ♡ ♡

  6. May 15, 2019 / 8:14 pm

    What a beautiful ring! I bet it's exciting that wedding planning is picking up. I've been married for 5 years this August and it wasn't a surprise to me haha, but that's okay, it didn't need to be!

    • May 16, 2019 / 4:49 pm

      LOL I love that!! Yes it feels more real every day. My wedding dress came in yesterday for example and that makes it feel even more real!

  7. FitFamilyLife
    May 15, 2019 / 8:51 pm

    Awww girl so exciting! Engagement memories are so special. We went on a jet to NYC and he proposed there! Was December and gorg and I will forever love NYC because of this!

    • May 16, 2019 / 4:50 pm

      *Gasp* OK that is amazing! What a guy you have!! A story for a lifetime for sure.

  8. Kasey
    May 15, 2019 / 9:32 pm

    I’m excited to read all your wedding posts. Thank you!

    • May 16, 2019 / 4:50 pm

      Yay! Good because I'm excited to share them.

  9. Jamaria
    May 15, 2019 / 10:33 pm

    What a lovely story! Congratulations girlie, enjoy this time because it FLYS by! xo

    • May 16, 2019 / 4:50 pm

      I will, or at least I'm trying to. =)

  10. Sunshineshopper
    May 16, 2019 / 12:34 am

    Congratulations Roxy! I am so happy for you!!

    • May 16, 2019 / 4:51 pm

      It's such a happy time for sure!!

  11. May 16, 2019 / 1:12 am

    Such exciting times! Congratulations! I love, love, love your ring!

    • May 16, 2019 / 4:51 pm

      Thank you so much Lily!

  12. May 16, 2019 / 1:16 am

    Such a beautiful post to read!! Your ring is absolutely gorgeous, congratulations!

    • May 16, 2019 / 4:51 pm

      Thank you Kileen! I adore the ring too.

  13. thesmalladventurer
    May 16, 2019 / 3:35 am

    I really love your story on how you became engaged! It's always interesting to look back and think about how life COULD HAVE been, but it's clear that the path you're on now is the one you're meant to be on! You've done you're growing and found a wonderful partner, and now you can go into marriage with excitement instead of uncertainty. Congratulations!

    • May 16, 2019 / 4:52 pm

      Such great points. I feel like if I'd married earlier it would have ended in divorce for sure. Of course there are no guarantees for the future in this life, but I feel like Alex and I have a nice solid foundation.

  14. Shari
    May 16, 2019 / 5:41 am

    Congrats and enjoy this time that leads up to your special day! I look forward to reading more details leading up to the big day (and we will be doing the sun dance although what ever the weather the day will be beautiful).

    • May 16, 2019 / 4:53 pm

      True! Although it would be much nicer to have our ceremony outside as planned in the sun or clouds than rain, lol! 😉

  15. tanviidotcom
    May 16, 2019 / 8:49 am

    I loved reading your story! So happy for you. Congratulations. That’s a beautiful ring.

    • May 16, 2019 / 4:53 pm

      Thank you so much Tanvii!

  16. Carol
    May 16, 2019 / 9:23 am

    Mazel tov and enjoy every moment!!!

    • May 16, 2019 / 4:53 pm

      I really am trying to soak it all in. It's been a near-constant stream of happiness for sure.

  17. She Saw Style
    May 16, 2019 / 9:37 am

    What a precious story! I totally understand the anxiousness surrounding when you wanted to get engaged. My husband surprised me like crazy, and I never knew it was coming, but I had suspected it for over 6 months, and that waiting is truly challenging haha! But it's worth it when the time is right!

    • May 16, 2019 / 4:54 pm

      Yes! In hindsight it all worked out perfectly, but at the time it felt excruciating! So funny how that works!!

  18. May 16, 2019 / 9:51 am

    What a sweet story!!! I had no idea my husband was going to propose when he did, but I knew he had the ring because I was there when he bought it LOL. I was 20 when he proposed back in 2015, he was 24. We only had a 6 month engagement but it was perfect for us!

    • May 16, 2019 / 4:55 pm

      LOL! I think that's lovely because you knew you were getting exactly the ring you wanted. Some guys are great at picking out jewelry while some guys…not so much.

  19. Chavi
    May 16, 2019 / 10:25 am

    My husband proposed to me in a hot air balloon at sunrise ❤️
    He set the bar high and his friends sort of hated him for a while ?
    We just celebrated 25 years together! I still can't believe it….
    Your ring is stunning and that pink lace dress is gorgeous on you! Mazal tov!

    • May 16, 2019 / 4:56 pm

      Oh my gosh that is epic Chavi!! What a great proposal!! Happy 25 years, that's amazing. ♡

  20. aisasami
    May 16, 2019 / 10:40 am

    Congrats on getting engaged, love that engagement ring!

    • May 16, 2019 / 4:56 pm

      Thank you very much!!

  21. Cindy
    May 16, 2019 / 3:49 pm

    Congrats!! Love your story. Wishing you great happiness and joy ahead!

    • May 16, 2019 / 4:56 pm

      Thanks so much Cindy!!

  22. May 16, 2019 / 4:27 pm

    Congratulations girl! Your engagement ring is absolutely stunning!! Enjoy the whole process.

    • May 16, 2019 / 10:14 pm

      Thank you! It's been 90% enjoyable thus far.

  23. May 16, 2019 / 4:28 pm

    Congratulations ?? my engagement was a surprise! And it was perfect. Just us and our doggie. So happy for you two.

    • May 16, 2019 / 10:14 pm

      Aww that's so sweet!! I love all kinds of proposals, from the intimate to the grand!

  24. May 16, 2019 / 6:32 pm

    I am so happy for you! Awww… what a sweet sweet story! I saw your bridesmaids dresses on your IG stories – they are gorgeous! xoxoxoxo

    • May 16, 2019 / 10:14 pm

      Thanks Cynthia! I know, I'm so excited to see them on my girls!!

  25. Renee
    May 16, 2019 / 6:37 pm

    Congratulations on your engagement! Your pictures are beautiful – I especially love the one of the two of you on the bridge.

    • May 16, 2019 / 10:15 pm

      Thank you Renee! Those are on the Brooklyn Bridge — I picked that spot for half our photos because he lived in Brooklyn and I lived in Manhattan when we met, and this was the midway point of sorts.

  26. gladmama
    May 17, 2019 / 5:15 pm


    • May 21, 2019 / 10:57 pm

      Thanks so much gladmama!

  27. Melodie
    May 17, 2019 / 6:36 pm

    Congratulations! Thank you for sharing your story. I look forward to the Wedding Wednesday series.

    • May 21, 2019 / 10:58 pm

      I think it's so fun hearing how people got engaged! I'm loving all the stories in the comments too.

  28. May 17, 2019 / 7:00 pm

    Oh this is such a sweet engagement story! Congratulations!! The best is to come!!!

    • May 21, 2019 / 10:58 pm

      Thank you Julia! I can't wait!!

  29. Helena Marz
    May 19, 2019 / 10:12 am

    What a lovely story…l love reading love stories on how people meet! Congratulations to both of you and your pictures are beautiful! All the best!❤️

    • May 21, 2019 / 10:58 pm

      Thanks so much Helena!! I agree, it's so fun reading people's romantic stories. I love the NY Times' Love and Vows columns for this reason!

  30. May 19, 2019 / 10:34 pm

    Wow congratulations! I love the hint of blue in that ring!

    • May 21, 2019 / 10:59 pm

      Thank you! It's more than a hint, it's a lovely sapphire that's a navy blue color!! 🙂

  31. May 20, 2019 / 6:41 pm

    Congratulations! What a cute engagement story and that ring is so pretty and unique!

    • May 21, 2019 / 10:59 pm

      Thank you so much Darleen!

  32. sewsarahr
    May 20, 2019 / 8:05 pm

    ahhh! congratulations to you both! That is wonderful news! XO

    • May 21, 2019 / 10:59 pm

      It's such a happy time for sure.

  33. May 21, 2019 / 9:09 am

    Congratulations! The best is yet to come. Marriage is beautiful! Love so much your history.

    • May 21, 2019 / 11:00 pm

      I can't wait! Even though we are engaged and already live together, there is something different about being married according to all of my married friends.

  34. Huda
    May 21, 2019 / 9:14 am

    How exciting! What an amazing time. Im glad youve had help from your friends and that ultimately you followed your heart when you felt too young to get married in your previous engagements. Good luck with everything going forward!

    • May 21, 2019 / 11:01 pm

      Thank you Huda! Yes it was difficult in the past to not really know or understand what I wanted, but now that I have what I want it's pretty dang amazing.

  35. May 21, 2019 / 10:24 am

    I am so excited for you!!! Marriage isn’t bliss, but it’s a helluva fun ride. Nothing quite like being able to hang with your best friend all the time.

    • May 21, 2019 / 11:02 pm

      Thank you Lauryn!! This may sound funny but Alex isn't my best friend. I feel like he fills a different role in my life (but do think it's very cute when couples feel their partner is their best friend). But I totally get what you're saying and yes I can't wait to officially be man and wife!

  36. May 21, 2019 / 10:52 am

    Such a sweet story! Your ring is stunning and the Brooklyn Bridge photos are magazine-worthy! *swoon*

    • May 21, 2019 / 11:03 pm

      Thank you so much Christie!

  37. katiethetourist
    May 21, 2019 / 12:49 pm

    Ahh so many congratulations – I'm incredibly happy for you!

    • May 21, 2019 / 11:03 pm

      Thank you!! It feels amazing to be in this season of my life. Finally. LOL.

  38. Rachel
    May 21, 2019 / 8:59 pm

    Congrats! What a sweet story. I can definitely understand the anxiousness of waiting for the ring when knowing it's coming, haha. I'm right behind you with my wedding in September. Exciting times!!

    • May 21, 2019 / 11:04 pm

      Oh yay congrats Rachel!! I hope that you too enjoy every moment of it — even the stressful moments!!

  39. Kait
    May 21, 2019 / 9:26 pm

    What I cute story! And I love your ring. My engagement ring is also non-traditional, since I have an aquamarine center stone. I love the bright pop of color in yours!

    • May 21, 2019 / 11:04 pm

      That sounds beautiful Kait! I have seen an increase in non-traditional rings lately and I think it's awesome. I love classic AND I love out there.

  40. May 21, 2019 / 10:36 pm

    Congratulations! This story is beautiful!

    • May 21, 2019 / 11:04 pm

      Thank you very much Amberly!!

  41. May 21, 2019 / 11:02 pm

    Oh my god, be still my heart!! That is beyond romantic!!

  42. May 22, 2019 / 12:15 am

    Your ring is absolutely gorgeous and I love your engagement story! Such an amazing time to get engaged during the holidays<3

    • May 23, 2019 / 8:16 am

      Oh my gosh it really added to the holiday magic in the end!!

  43. Bbb
    May 22, 2019 / 7:02 am

    Thank you so much for sharing! Congratulations to you both!

    • May 23, 2019 / 8:16 am

      It's so much fun to share the story with longtime readers like you Bbb!!

  44. evb
    May 22, 2019 / 5:24 pm

    One of your best posts ever, Roxy, I so look forward to seeing all your wedding Wednesday posts!

    • May 23, 2019 / 8:17 am

      Thank you so much evb!! ❤️

  45. Deanie
    May 24, 2019 / 11:23 am

    Oh my goodness!! CONGRATULATIONS!! Such an excited time!!

  46. Nam
    May 31, 2019 / 9:18 pm

    Wow❤️❤️❤️❤️❤️❤️❤️❤️❤️ Congratulations Thea oops Roxy??

    So happy for u!!!!

    Absolutely love everything u wrote and pictures u posted…….. looking forward to see ur wedding pics Roxy!

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