That time I was pregnant and I met Oprah | And that interview last night

Let me tell you about the time I met Oprah, and then let’s chat a bit about that interview last night with Meghan and Harry!

How I came across these photos

During the Toronto lockdown, I added a folder on my computer titled “House Prints Enlargements” because I’m going through vacation photos to see what might make the cut for printing.

I came across these absolute GEMS which will not be enlarged but I thought I’d blog about them so that I’ll always remember the story. It’s also fun to tell!

That time I met Oprah Winfrey in Chicago | Jessica Nip Photography | info@jessicanip.com

A vacation before baby arrived

I was about 5 months pregnant and this Chicago trip would be our last vacation before our baby arrived. Like many people, we ate our way through Chicago: Frontera Grill, Alinea, Topolobampo, a few hot dog restaurants I can’t remember the names of, and of course trying their famous deep dish pizza. We also attended a baseball game at Wrigley Field and ate our first philly cheese steaks, toured some Frank Lloyd Wright homes, went on a river boat cruise (which was amazing and so informative!), got caught in the middle of a Transformers movie filming, and “bumped into” Barack Obama’s motorcade as it was arriving at a building (I don’t remember where, I just remember we were walking around and suddenly saw a lot of security and snipers on rooftops!)

The planned outing

But the highlight was meeting Oprah. My friend, Jen, was in town visiting her brother so we planned a trip out to the area where Oprah’s studio was. We wanted to take a photo out front and then visit the gift shop to pick up some Oprah souvenirs (we are BIG fans!)

Let’s just say my husband came along but thought the whole thing was SILLY, taking an expensive cab ride out of downtown JUST to take a photo in front of a sign.

What happened next

When we arrived at the studio, we took our obligatory photo in front of the studio sign and then wandered around trying to find the gift shop. NO ONE was around as it was the middle of the day in an industrial area. We couldn’t find anyone to ask for directions; this was pre-smartphone days so searching online was not an option!

So we wandered.

Then, we spotted some figures exiting another building across the street so we headed towards them to ask for directions. Those three figures turned out to be Ms Winfrey herself with what I assume were two bodyguards.

Meeting her

I don’t remember very much about the next 5 minutes, only that Jen and I couldn’t stop crying. Ms Winfrey shook our hands and asked if we’d like some photos taken and if so, could we walk across the street with her because she thought the corner by the studio was the better backdrop.

She then proceeded to pose for photos with us, even suggesting that my husband hand the camera over to one of her bodyguards so that he could be in the photos, too! It was a moment that none of us, including my husband, will ever forget.

She was so gracious and patient.

What happened after

We must have stood there on the corner for a good 5-10 minutes afterwards crying and commenting how unbelievable the whole encounter was! We eventually did make it to the gift shop, after asking Ms Winfrey where it was before she left us.

I’m so glad we have photos of this moment – every time I look at them I’m transported back to this moment in time that I will always cherish!

On the Meghan and Harry interview last night

Did you watch? What did you think? I always love watching Oprah interview her guests. She has such an ease and grace about her. I mean, she is one of the greatest interviewers of all time, and I don’t think I’m the only one who holds that view!

During last night’s interview, I felt her questions got right to the point and I appreciated how she asked what many viewers were probably thinking in certain moments. AND THAT BACKYARD! Who’s backyard was it, and can I please have a tour?!

How will the British press react?

A lot of information bombs were dropped last night by Meghan and Harry, and I can’t help but wonder how this will be reported on in the British press. I personally think they are going to fire right back at them with hurtful and accusatory headlines. They love their monarchy and will defend it against all costs, after all (at least, this is what I believe).

Wouldn’t it be so amazing if Oprah could sit down with the Royal family and get the other side of the story? I know, I know, this would never happen in a billion years.

What do you think of it all? Comment below or send me a DM on instagram!


Jessica Nip Photography specializes providing a full service experience that starts with booking your session through to the beautiful tangible heirloom products being displayed in your home. Her style of soft, natural and light-filled imagery can be seen in all her maternity, newborn, child and family portraits in Toronto, Canada. Her favourite images are highlighted on the blog, but if you’d like to see what a full gallery looks like, please send her a note and she’d be happy to show you!

To inquire about a session, please click here or email Jessica at info@jessicanip.com.

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