Date Night on The Roof

Do you dress up for date nights? I usually don’t—jeans and T-shirts are my uniform—but recently I’ve been trying to put in a little more effort. So when White House Black Market offered to send a dress to try, I said an enthusiastic yes. This week, we had drinks on our building’s roof deck and then went for dinner. Here are a few photos, if you’d like to see…

Alex’s signature drink is a Negroni—which reminds him of our honeymoon—so he mixed two up for us to sneak onto the roof. (And thanks to Yossy, who stopped by to take a couple photos.)
The roof deck looks over the Hudson River, and the views are pretty gorgeous when the weather is nice, especially when the sun is setting. We’re trying to take full advantage of it before we move in August. It was fun to dress up—I chose a dress from their “Ultra Slimming” line, which has built-in shapewear and asymmetric tiers. And, I have to say, I loved seeing Alex in a jacket and tie. (Also, in the very top photo, above, we were laughing because he made me take off my heels so I’d be shorter than him, haha.)
The view! Afterward we walked to a little Italian place in our neighborhood (thank goodness for the built-in shapewear:)

What about you? Do you dress up on date nights? I’m trying to try a little harder! It feels good and makes it feel like a special occasion. You can see all the White House Black Market dresses here, if you’d like.

P.S. Fire-escape drinks, and a trapeze class.

(Thanks again to Yossy Arefi for coming over and taking a few photos! This post was sponsored by White House Black Market. Thanks for supporting the brands that support Cup of Jo)

  1. My boyfriend and I live together and currently are working on the same project as well. We see each other at work and back home tired every day. We sit around in jammies n eat our meals on our bed even though we have a living room. So definitely big YES, we totally dress up for our dates. Sometimes together, where we then end up trying to outdo each other in looking better or a few times may not make it out of our house for cuddly romantic reasons. And other times we give each other space to get dressed and meet outside our home.
    Both times my bf always pretend sulks that I dressed myself better then him.
    So yup, getting all cute for dates is a , must for us.

  2. That looks like fun! Your rooftop view is gorgeous. My husband and I just moved to Seattle, and we are in an apartment with a rooftop. It’s so much fun to go up there!

    Good for you for spicing up your date night and doing something extra fun. ;)

  3. You guys look fantastic. Love your comments about the awkward photography feeling. My husband is esp terrible at that sort of thing… one of my bridesmaids ended up going on a date with our wedding photographer afterward, and his only complaint about working our wedding was how hard it was to get my husband to smile in a way that isn’t totally creepy/weird.

  4. I am feeling inspired! I always feel awkward and inauthentic when I dress up more than my usual uniform, like people will look at me and think I’m trying too hard or not being myself or something.. even strangers! It’s so silly and I love how I feel when I make more an effort to look nice, so I’m trying to be better about owning it and just being confident and not caring about what anyone thinks. Except maybe my beau!

  5. leah, haha, good question! sometimes it’s funny/awkward like when we took photos of at-home massages for a sponsored post! but we’re good friends with the photographers we work with, so it just ends up being funny.

    funnily enough, in general, i actually feel like we take very few photos of our life overall—just every couple weeks for the blog. there are a gazillion many personal moments in our everyday lives that we don’t photograph or write about, so these kinds of photo shoots actually feel very few and far between to me, and feel more like funny moments to snap quick pics before we have our actual date! hope this helps answer the question!

    thanks so much for writing,

  6. Now I’m curious… how tall are you both?

  7. A.) My husband and I have only been on like 3 date nights since we had our son almost TWO YEARS ago. Yeesh. We gotta get out more! And I’m totally dressing up next time we do.
    B.) You look amazing. Love the dress!
    C.) The view!!!!! How sad that you’ll have to leave it behind when you move. I imagine it’s so peaceful to live near water like that.

  8. I’ve always wondered if it ever gets weird to constantly have to take photos and pose for the blog, especially during such intimate/private moments between you and Alex….thoughts? beautiful shots though by the way- as always!

  9. ooo i love those heels!

  10. Cute!! I want a dress with built-in shapewear! That’s genius.

    That’s hilarious your husband made you take your shoes off. :)

  11. you look absolutely lovely!

  12. What an incredible view! Treasure it, and treasure these rare date nights.

  13. My husband and I have been married about a year and a half, with no kids, so we still find movie nights at home and trips to the grocery store pretty exciting, so neither of us dress up for those. My favorite date recently is going to the farmer’s market Saturday morning and I do try to wear something summery and flirty for those.

  14. Agree with the others – you look lovely! These days I’ve been pretty lazy when it comes to dressing up. I think I will wear a dress to dinner tonight! :)

  15. All men are the same 😊 my husband some times gets obsessive with my high heels too.
    You look lovely by the way 👍
    And I must say that I’ fell in love with you roof top view 😍

  16. You do look awfully pretty! (And you don’t need the shapewear a bit, although it’s always nice after pasta!) I can never get over how men love a pretty dress.

  17. oh and thank you for asking about how i stay healthy. i don’t really have any tips—i am ALWAYS thinking i should do more, especially when it comes to strength/flexibility/etc. i am the worst at that stuff! i do walk and bike pretty much everywhere (partly because i’m phobic of subways!), so that helped for losing the baby weight, plus i have a certain chubby baby who always want to be carried:) other than that i try to eat generally healthy foods and not drink tooooo much wine, although sometimes that cannot be helped:) joannaxoxo

  18. One time the BF and I went on an impromptu dinner date and he came into the bedroom after waiting for me to get dressed and said, “What are you getting all dressed up for? It’s just dinner in the neighborhood!”


  19. I LOVE the detail of his signature drink. How sweet!

  20. you guys are so sweet to say we look relaxed! we always feel a little awkward, honestly :)

  21. hi!!! sorry for the slow reply, and thank you so much for the lovely comments. the shoes are from loeffler randall, a few years ago. thank you so much!

  22. Absolutely gorgeous! Sure the hubs liked it :) Although you would look beautiful in t-shirt/jeans combo! Adding just a little extra is always worth it though!

    XO Chloe A Latte Lipstick

  23. You look amazing! You and Alex make such a great couple :)

  24. Gorgeous dress! I love it. I bought a LBD from CK a few weeks ago and I’ve looked at WHBM dresses and swooned. Beautiful!

  25. You look fantastic.

  26. When our youngest got old enough for a babysitter, we started going out as a couple 1-2 times a month and it’s usually a dress up thing! So much more fun, the getting ready, discussing where we’ll go and what we’ll wear… :)

  27. Thank you for this post. I’m in the middle of a very stressful event for work and you made me smile during this quick minute to myself!

  28. You look so happy (which guarantees you look so pretty too). Sweet pics.

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  30. A question for you, Joanna. How do you and Alex take such natural, relaxed-looking photos? Does it all come down to having good relationships with your photographer? Lots of practice? Or something else? You guys (Toby and Anton,too) always look so at ease.

  31. Joanna, you’re one gorgeous lady, and together with Alex you’re a great looking couple. I’ve always loved seeing glimpses of how you keep “dating” after being married for a couple years, such a nice piece of inspiration once I find the right person down the road. I’m appreciative as ever for your NYC posts in the archives for when I move to Purchase (just a bit further north) next month for school as a great source of ideas for fun things to do in the city over weekends. I’d love to read a post someday of a few of your favorite things to do/places to go either by yourself or with friends in the city. Just an idea! And great photos, btw. :)

  32. I don’t always dress up for date night, but whenever I do it feels more special and more like a date. These pictures are so cute, I love that he made you take off your shoes ;)

    Kristina does the Internets

  33. The photos are lovely! New York looks beautiful, would love to live in such a pretty city. I love to dress up on nights out, especially as it gives me a chance to go all out on my makeup and add a bright lip as I tend to keep my make up very naturaul day to day

    The Internationalist

  34. that dress looks beautiful on you!

  35. You really look smokin’ in that dress. Makes me want to run out and get it too. What a great testimonial for the store!

  36. Great dress! I like the idea of built in shape wear, particularly 3 months after having my little girl! I’ve tried dressing up for date nights, but furthest I ever get is a little makeup.

  37. I definitely agree with the other commenters who would like to hear about what you eat/do to stay so trim! You both look great :)

  38. Impressed by the dresses, they are actually reasonably priced! I was thinking they’d all be at least $300.

  39. aw how I love the pictures I miss NYC! black is wonderful on you as any other color you have such a nice carefree look. As far as answering your question, no I don’t, now that im on the west coast and him the east i think we will have to do it via skype and I will make an effort to dress up!! lovely post.

  40. Those shoes are adorable — do they have lime green on them? So much yes! Where do I get some? :)

  41. Also, you look FANTASTIC in that dress!

  42. I definitely dress up on date nights. I either put a nice dress on or some jeans with a cute top and heels. I think that it makes the night even more special, and feels like we’re going on a first date. So I definitely try to do my best whenever we have date nights. By the way, those pictures are beautiful! Stunning :)

  43. Girl, you look gorgeous!!

  44. this is so sweet! and lovely! I would take ffuullll advantage of that while you can! My husband and I always (maybe, almost always) dress up for date night! If we are going out, we have a getting ready ritual: We have separate bathrooms, so it’s a surprise when we see each other. But, we pour a drink, and put on some tunes, and I have to imagine we are both dancing in our bathrooms!

  45. An intimate rooftop date, just the two of you…& the photographer. At least you have a spectacular view. :] // itsCarmen.com ☼

  46. So jealous of your rooftop! We live up in Inwood and have amazing views even from our first floor apartment (overlooking Inwood Hill Park and the Harlem river), but they won’t give us rooftop access for what I’m sure is an even more stunning view. Coops can be such jerks. Ha.
    Enjoy it for us all!

  47. Those are lovely photos, which capture the love you two have for each other.

  48. What brand/style are your heels? Love them

  49. Ahh, you look so good in that black dress. I can’t believe you’ve had two kids!

  50. Ahh, you look so good in that black dress! I can’t believe you’ve had two kids.

  51. Joanna, you’re totally gorgeous. (And you and Alex make a great looking pair!) Glad you had a fun date night, and thanks for all your NYC ideas on the blog. I can’t wait to look through your archives for NYC weekend inspiration when I move to Purchase (just a teeny bit further north) next month. I’d love to read a list someday on what you’d recommend doing over a long weekend, or something along those lines. :)

  52. that view is right! jersey city is a pretty cool place ;) but in all honesty, you need to see the sunset from the OTHER side of the Hudson too. on a clear night, the sunset reflects on the glass manhattan skyline and is one of the most beautiful scenes…

  53. You guys look lovely. Joanna I love ur dress but can’t seem to find it on their site. Also where r your sandals from?

  54. Ok, I am sure 500 people are going to say this, but you look amazing in that dress!! I think you need to do a post about how you stay so healthy despite running your own business, and running after 2 boys!

  55. I love those shoes you are holding in the top pic! Very cute :).

  56. Beautiful photos and love the dress. I always try to dress up for date nights, nothing too much, but always try to be cute. And of course, always a fun lipstick and a bit of make up. Xx

  57. Who are your shoes by? They are adorable.

  58. I like ur dress but don’t see it on their site. Also where r ur sandals from?

  59. Such pictures. Very class. Much drinks. Wow!