Tiffany Haddish's Celebrity Crushes: From Toby Sandeman to Giancarlo Stanton (2025)

Picture this: a hilarious comedian turning a TV chat into a bold flirting spree with a star baseball player, all while the cameras roll and laughter echoes! It's the kind of celebrity moment that has everyone buzzing, and today we're diving into Tiffany Haddish's latest adventure on Today with Jenna & Friends. But here's where it gets controversial: is this just playful fun, or could it spark real sparks? Stick around to find out what happened next – it's the part most people miss in these viral clips.

Tiffany Haddish, the witty actress and comedian known for her spot-on impressions and larger-than-life personality in films like Girls Trip and The Emoji Movie, made a return appearance on the show. This time, host Jenna Bush Hager, daughter of former President George W. Bush and a beloved figure in daytime TV, had a surprise up her sleeve from Haddish's previous visit. Back then, Haddish had expressed her crush on Toby Sandeman, the charming actor from the series Running Point, and Jenna arranged a video message from him. It was a sweet gesture that left Haddish beaming – and now, she was back for more.

During this latest chat with Jenna and co-host Carson Daly, the laid-back TV personality and former American Idol host, Haddish decided to aim even higher. She boldly declared her interest in Giancarlo Stanton, the powerhouse right fielder and designated hitter for the New York Yankees. 'I'm also trying to woo Giancarlo Stanton, jersey number 27 from the New York Yankees,' she announced, drawing chuckles from her hosts. To put it simply for those new to the sports world, Stanton is a superstar slugger whose home runs have thrilled fans in baseball's biggest league.

Haddish kept the humor rolling with a joke about her attempts to reach him. 'I've noticed his phone number's changed. He hasn't been answering my calls,' she quipped, poking fun at the idea of a celebrity ghosting – something many of us have experienced in dating, right?

But Jenna wasn't afraid to tease Haddish about her past. She brought up that infamous photo Haddish shared with actor Jason Lee, which tricked the internet into thinking they had a baby together. Carson, always the quick thinker, suggested a cheeky way to grab Stanton's attention: 'Why don't you post a picture of a baby in a Yankees jersey with number 27 and just leave it at that?' It was a playful nod to viral stunts that can go hilariously wrong – or right.

Haddish fired back with her own twist, imagining a scenario that could really turn heads. 'I feel like nobody’s gonna get that, but if it’s me and Giancarlo Stanton standing together, and I’m holding my belly like, 'Cat's in the bag!'' she said. This kind of creative, over-the-top flirting is classic Haddish, blending comedy with a bit of fantasy. And who knows? Stranger things have happened in Hollywood.

Interestingly, Haddish's charm seemed to work before with Sandeman. After publicly fawning over him as her celebrity crush, they were spotted out and about together. They even coordinated Halloween costumes inspired by the sci-fi thriller Severance, dressing as characters Mark and Helly – a fun example of how crushes can lead to friendships or more. Haddish, however, was quick to clarify they weren't an official couple. 'He’s not ugly, I can tell you that much. I like beautiful friends,' she told Jenna, adding, 'We’re just pals, but you know how I work.' It raises an intriguing question: where's the line between flirting for fun and something more serious? Is Haddish just keeping it light-hearted, or testing the waters?

Jenna certainly played matchmaker by putting in a good word. During Haddish's guest-hosting stint on the show in April, Sandeman popped up with a heartfelt video message. 'A little birdie told me that I’m your favorite character on Running Point,' he said warmly. 'Always did think you had great taste. I’m in Ireland right now, but I wanted you to know that I will be tuning in and rooting for you. Now before I go, let’s take care of a little business. I think we need to get you on Running Point to play my wife. What are your thoughts?'

Haddish was over the moon, jumping at the opportunity. 'Yes, I do. I do, and I do!' she exclaimed. 'We can play pretend and we can play for real. I just, oh my goodness. I think that was beautiful! I’m gonna call Kate Hudson and say, 'Girl, he offered me a job!' I think I need to get a ticket to Ireland. We’ve gotta do a chemistry test!' It's a perfect illustration of how a simple crush can evolve into exciting professional possibilities – who wouldn't want to act alongside their favorite star?

Today with Jenna & Friends airs on weekdays at 10/9c on NBC, so tune in for more of these entertaining celebrity chats.

But here's the controversial twist: some might say Haddish's public flirtations cross into cringe territory, while others see it as empowering women to pursue their dreams boldly. What do you think – is this harmless fun or a recipe for awkwardness? Do celebrity crushes ever lead to real relationships, or are they just tabloid fodder? Share your thoughts in the comments below – agree, disagree, or share your own crush stories!

Tiffany Haddish's Celebrity Crushes: From Toby Sandeman to Giancarlo Stanton (2025)

References

Top Articles
Latest Posts
Recommended Articles
Article information

Author: Errol Quitzon

Last Updated:

Views: 5697

Rating: 4.9 / 5 (59 voted)

Reviews: 82% of readers found this page helpful

Author information

Name: Errol Quitzon

Birthday: 1993-04-02

Address: 70604 Haley Lane, Port Weldonside, TN 99233-0942

Phone: +9665282866296

Job: Product Retail Agent

Hobby: Computer programming, Horseback riding, Hooping, Dance, Ice skating, Backpacking, Rafting

Introduction: My name is Errol Quitzon, I am a fair, cute, fancy, clean, attractive, sparkling, kind person who loves writing and wants to share my knowledge and understanding with you.