it was over two weeks ago when gina and i ventured to chicago to see Oprah yet i’m still glowing from the experience. hands down, it was one of the most fun weekends of my whole entire almost 36 years. i have no idea why i didn’t take more photos!

do you mind if i give you the entire scoop, detail by detail? i want to re-live every moment.

elysian-hotels-resorts-images

(photo from hotel website)

saturday: we arrive in chicago. no plane drama or delays. during the plane ride, i felt strange to be leaving True and John behind but also ready for some real deal fun. i slept most of the plane ride (middle seat – ugh) and i was also looking forward to more uninterrupted sleep in a hotel room. bliss.

we arrive at the elysian hotel. holy smokes, this place is NICE. in fact, i’ve never stayed at a nicer hotel before. a friend told me about their winter getaway package and after realizing they had a full spa on site, gina and i were sold. major splurge and worth every penny. the service was amazing, fresh flowers everywhere, the most luxurious bathroom/tub i’ve ever seen. they even came by our room in the evenings to “turn down” the room with fresh water by the bedside, a printed card with the next days weather forecast, curtains closed, mood lighting, the works. omg!

after walking around downtown for a bit, we had dinner with two new friends at a delicious restaurant (can’t remember the name) in a neighborhood not too far away. it was great to eat at a local neighborhood restaurant and chat over really delicious food. i felt so far away from my life in good ways. to be eating out at a restaurant at night felt indulgent!

that night i slept HARD and for something like 9 hours. ahhhhhh….

sunday: gina and i treated ourselves to a morning at the hotel spa complete with hour long massages, soaks in the whirlpool and more. totally relaxed, we ate another delicious meal at a local restaurant (italian!). i remember having a couple of vanilla lemondrops. total indulgence.

after our big meal, we headed to Harpo Studios for a personal tour! yes, a personal tour! it turns out that many of you wrote to the oprah show on my behalf (seriously you guys? THANK YOU) which led to a producer offering us a personal tour. can you seriously believe it? i could not. thank you, you know who, for setting this up. i can’t tell you how amazing it was to see behind the scenes – things like the control room, the offices where all the producers do their work, where Oprah’s office was (it’s right there with everyone else’s!), the actual tv set (WAY smaller than it looks on tv which means every seat is a great seat), and so much more.

gina and i were amazed by how normal it all seemed – like any other office environment. it’s funny to think that it would be any different but it really wasn’t. it’s the people who work there that make it spectacular, not necessarily the office building or even the set. after our tour, the producer (who was DELIGHTFUL) sent us home with a few oprah tokens including hats, tshirts, and mugs. really FUN and we felt incredibly lucky. after that, we went back to the hotel and were in bed by 9pm. i slept for 12 hours straight. heaven.

monday: the big day! we get dressed. by the way, i went to nordstroms two days before leaving for chicago to find an outfit. i had NO idea what to wear. i told the ladies who worked there that i was heading to oprah and stressing about what to wear and they scooped me up into a big and fun two hour adventure of finding just right thing. danella styled me head to toe with boots, jeans, shirt, sweater, belt. above is what i wore (not the best photo but you get the idea).

for the show, it turns out i was not under dressed nor was i over dressed. i was comfortable and feeling sassy in my new discovery of boots over jeans (now addicted!). there were people super dressed up and there were people super dressed down. gina and i were in the middle.

the hotel driver gave us a complimentary drive to harpo studios in a car that massaged our backs. no lie! i had no idea these options existed. we felt so fancy in our new outfits in this fancy car that massaged our backs on the way to oprah. we kept looking an each other with the are you kidding me? expressions and the omg, can you believe this? and the holy shit, we’re in chicago for an oprah show! we did this all weekend long. it was so fun.

we arrive at the show and we’re at the end of the line. a woman calls out our names and takes us up to the front of the line and to the place where we check our coats. i have no idea how our name got on her list, but it was really fun to skip everyone in line and get out of the cold (i feel so bad for saying that!).

after checking our coats, we head up to a big seating room that has big photos of oprah and famous people all over the walls. we sit there for about an hour. gina and i are in people watching heaven. all those outfits! and personalities! and chitter chatter! at this point, we all know that we’re at the diana ross show and the room is full of diana uber fans. at one point, this big dude in nice pants and a pink button down shirt leads the whole entire room (a hundred people, maybe?) in singing well known diana and supreme songs. so much fun. gina and i were into it.

after awhile, they start calling names to be seated. like i said before, the set is SO MUCH SMALLER in person than it is on the tv screen so any seat is a great seat. we were in the front row of the middle riser – the part where the seats begin stadium style seating. we felt so close to the stage, so close. it was awesome.

the audience warmer upper comes out and she gets us all standing and dancing and screaming while the black eyed peas are on the speakers. really fun. she reminded us that we WERE AT THE OPRAH WINFREY SHOW and to really celebrate that with the person we came with. she had us jumping up and down, hugging one another, and screaming things like WE’RE AT THE OPRAH WINFREY SHOW! hilarious….

finally, oprah comes onto the set. we all go nuts. i’m not kidding, i started to cry. i do not know what came over me. i’m not normally a person who goes gugu gaga over such things or people but i was so overcome with the entire experience: how we got the tickets, how much my life has changed in five months, how it feels so good to scream and dance and be silly, how kindness has changed everything, how gina and i are there together, how i’ve never felt more pampered by a getaway weekend, how spoiled i feel to be there, how OPRAH WINFREY is standing just over there.

the cameras aren’t rolling yet but oprah thanks us for coming and she begins to tearfully tell us the story of how diana ross gave her hope as a 10 year old black child. she talked about how we all want to belong and find our tribe and how seeing a young black diana ross on the television when she was 10 years old made her feel a sense of belonging. i cried some more. it’s so true. we must find our tribes. i was struck by how honest oprah was telling us this story and how i want to be just like her when i grow up. i was also struck by how we are all just people being inspired by other people. in some small way, oprah is to me how diana ross is to her. maybe that explains my tearfulness when i saw her walk onto the set.

the cameras start rolling and diana ross enters the studio singing her hit song, i’m coming out, and we all go crazy. diana ross is right there. right there! singing! and she looks amazing. and isn’t she in her 60s? and omg, i cannot believe i am here.

what i loved most about diana ross is all the the things she said about being a mother. whenever oprah asked her anything about her success in music, movies and so forth, diana ross would always come back to how being a mother is what has made her feel abundant in joy and successful at living – that motherhood was her biggest accomplishment and where she has done her greatest work. loved hearing this.


liv – who also sings “you are my sunshine” to her child (who is also named True but without the e) sent this over to me the day before i left for chicago – chuckle.

it was so interesting to watch what happens during the commercial breaks. oprah chatted with diana and her family (her five kids were with her), and staff members. at one point, i kid you not, oprah said “kelly? where’s kelly?” and i nearly jumped out of my seat, here i am, right here! for a split second, i thought this might be my surprise moment, the moment when oprah comes over and tells me that she’s going to make one of mondo beyondo’s come true, the moment she tells me that she’s been reading my blog, seeing my artwork, etc, etc! it was only a split second, but it was HILARIOUS how wrong i could be! “kelly” it turns out was one of her production staff :). see what i mean? i. am. crazy.

toward the end of the show, oprah gives the entire audience a brand new samsung galaxy tab. it was so seriously fun to be inside a moment that you see on her show all of the time – the one where everyone is screaming and jumping up and down because oprah gave them something. because the screaming was so loud, i had no idea what we got but i was screaming and jumping anyway. what i love about those moments on oprah is that it’s not really about the thing she’s giving a way. it’s more about the moment, the few seconds where you feel like a kid on christmas morning instead of the adult that you are, the new mama that you are, the struggling parent that you are, the overworked employee that you are. it was glorious, that moment. gina and i screamed in glee.

the show ends and oprah walks off the set with diana ross. and just like that, it was over.

we hop in a cab with our glee and head to the airport where we part ways and return home to our families. i will never forget those few days in chicago where fun and surprise and sassy outfits and good food and pampering and connections took place. it was, hands down, one of the best weekends of my life. thank you to all the people who made it possible: megan, allyson, liv, those of you who wrote the show (!!), the folks at the hotel for pampering us, and to gina for sharing this remarkable experience with me. we did it! we went to an oprah showwwwwwwwwwwwwwww!

Hi, I'm Kelly Rae Roberts!

Before I picked up my first paintbrush at the age of 30, I was a medical social worker. I followed my whispers and started playing with paint and everything changed. Now I’m a full-time artist, author and Possibilitarian, who helps women explore their creativity, nourish their souls and build a thriving creative business.

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