MomSkoop
Even the biggest stars in Hollywood face rejection when it comes to romance.
From awkward dinner invitations to ignored text messages, famous folks have been turned down just like the rest of us.
Sometimes the chemistry just isn’t there, or the timing is all wrong.
These stories prove that fame and fortune don’t guarantee success in love, and that even celebrities have to deal with the sting of hearing “no thanks” from someone they’re interested in.
1. Drake and Nicki Minaj
Drake has never been shy about his feelings for Nicki Minaj, and he’s openly discussed his failed attempts to win her heart.
The rapper tried multiple times to turn their friendship into something more romantic, but Minaj consistently kept things platonic between them.
Their close working relationship made things complicated.
Fans watched their chemistry in music videos and performances, hoping they’d become a couple.
Drake even proposed to her during an MTV Video Music Awards appearance, though it was part of a staged moment.
Despite his efforts, Nicki made it clear she valued their friendship over romance.
She’s mentioned in interviews that mixing business with pleasure wasn’t her style, especially with someone so important to her career and personal life.
2. Chris Rock and Rihanna
Comedian Chris Rock shot his shot with Rihanna, but the rejection stung in a particularly memorable way.
He later joked about the experience during his stand-up routines, saying she looked at him like he was an aunt trying to give unwanted advice at a family reunion.
The age difference between them made the situation even more awkward.
Rock was old enough to remember when Rihanna wasn’t even born yet, which probably contributed to her less-than-enthusiastic response to his interest.
Rock handled the rejection with humor, turning it into comedy material.
His willingness to laugh at himself made the story less painful and more entertaining.
Rihanna never publicly commented on the situation, keeping her dignity intact while Rock got some great jokes out of the experience.
3. Justin Bieber and Jennifer Lawrence
Jennifer Lawrence didn’t mince words when asked about Justin Bieber’s interest in her.
She gave what she called a hard no, making it crystal clear there would be no romantic future between them.
Lawrence’s blunt honesty became legendary among fans who appreciated her straightforward approach.
Bieber was at the height of his teen heartthrob status when he expressed interest.
Lawrence, however, was focused on her acting career and wasn’t interested in dating someone younger.
The age gap and their different life stages made them incompatible in her eyes.
Lawrence discussed the rejection during interviews with her trademark humor.
She never seemed mean-spirited about it, just honest about her preferences.
Bieber moved on quickly, as young stars often do in Hollywood’s fast-paced dating scene.
4. Niall Horan and Katy Perry
When One Direction’s Niall Horan tried to catch Katy Perry’s attention, she gently let him down by saying he was too young for her.
Perry was already an established pop star when Horan was just beginning his career with the boy band, making the age difference significant.
Horan reportedly had a major crush on Perry during his early fame days.
He wasn’t alone among his bandmates in admiring her, but he was brave enough to actually make his interest known.
Perry’s response was kind but firm, showing maturity in how she handled a younger admirer.
The rejection didn’t damage either of their careers or reputations.
Both continued to thrive in the music industry, occasionally crossing paths at awards shows and industry events without any lingering awkwardness from the failed flirtation.
5. Jake Gyllenhaal and Jessica Biel
Before Jessica Biel became Mrs. Justin Timberlake, Jake Gyllenhaal tried to ask her out in the early 2000s.
Biel politely declined his invitation, and both moved on to date other people in Hollywood’s interconnected social circles.
Gyllenhaal was already gaining recognition for his acting talent at the time.
Biel was riding high on her success from television and transitioning into film roles.
Their paths crossed at industry events, but romantic chemistry just wasn’t there for her.
Looking back, the rejection worked out well for everyone involved.
Biel found lasting love with Timberlake, while Gyllenhaal went on to date several other high-profile celebrities.
Sometimes a no leads people exactly where they’re supposed to be, even if it doesn’t feel that way initially.
6. Harry Styles and Lindsay Lohan
Harry Styles reportedly tried his charm on Lindsay Lohan at a party, but she shut down his advances with a simple excuse about needing sleep.
Lohan later shared the story, explaining that she politely rejected the much younger singer without making a big scene.
Styles was still with One Direction and just starting to explore his famous heartthrob status.
Lohan had already been through the Hollywood wringer and wasn’t interested in dating someone so much younger.
Her response was diplomatic, giving him an easy out while maintaining her boundaries.
The interaction became a funny anecdote rather than a scandal.
Both celebrities laughed about it later in interviews, showing that sometimes rejection can be handled gracefully.
Styles certainly didn’t let one no slow down his romantic adventures in the years that followed.
7. Nicole Kidman and Jimmy Fallon
This rejection story is unique because Jimmy Fallon didn’t even realize he was rejecting Nicole Kidman.
She came to his apartment years ago hoping for a romantic connection, but Fallon thought she was just visiting to discuss a potential project.
He spent the whole time acting awkward and barely paying attention to her.
Kidman later appeared on Fallon’s talk show and told the embarrassing story.
His face turned bright red as she explained how she’d been interested in dating him, but he completely missed all her signals.
Fallon was mortified, realizing he’d accidentally rejected one of Hollywood’s most beautiful actresses.
The story went viral because of how genuinely oblivious Fallon had been.
Viewers loved seeing the usually confident host squirm with embarrassment while Kidman laughed about the whole situation.
8. Demi Lovato and Emily Hampshire
Demi Lovato slid into Emily Hampshire’s DMs hoping to start a romantic connection, but Hampshire politely turned down the invitation.
Lovato was brave enough to make the first move through social media, a modern approach to celebrity dating that doesn’t always work out.
Hampshire, known for her role on Schitt’s Creek, handled the situation with grace.
She later mentioned the interaction in interviews without being mean or dismissive about Lovato’s interest.
Both celebrities seemed to understand that attraction isn’t always mutual, even between famous people.
The DM rejection shows that even celebrities face the same dating challenges as everyone else.
Getting left on read or politely declined happens to stars too.
Lovato moved forward without dwelling on the rejection, continuing to be open about their dating life and preferences.
9. Julianne Hough and Daniel Radcliffe
Julianne Hough sent Daniel Radcliffe a Valentine’s Day card hoping to spark some romance, but she never received a response.
The card went unanswered, leaving Hough to realize that Radcliffe either wasn’t interested or never actually got the message.
Hough was already famous from Dancing with the Stars when she made her move.
Radcliffe was transitioning from his Harry Potter days into more adult roles.
Their careers were both thriving, but romantic timing just wasn’t on their side.
She later talked about the unreturned Valentine openly, showing she could laugh at herself.
Radcliffe may not have even known about her interest, which happens sometimes with celebrity crushes.
The lack of response was probably more about logistics than personal rejection, but it still counted as a no by default.
10. Brooke Shields and Donald Trump
Before his presidency, Donald Trump asked Brooke Shields out on a date, and she publicly declined.
Shields recounted the story in interviews, explaining that Trump’s approach didn’t appeal to her and she had no interest in going out with him.
Shields was already an established actress and model when Trump made his move.
She’d been famous since childhood and had dealt with plenty of unwanted attention over the years. Trump’s persistence didn’t sway her decision to say no.
Her willingness to share the rejection story publicly showed confidence.
Many celebrities stay quiet about turning down powerful people, but Shields didn’t hesitate to be honest about it.
The story became more widely discussed after Trump entered politics, giving it renewed interest among fans and media.
11. Salma Hayek and Donald Trump
Salma Hayek also found herself on the receiving end of Donald Trump’s romantic interest, and like Shields, she turned him down.
Hayek shared her experience publicly, describing how Trump had pursued her despite her clear lack of interest in dating him.
Hayek was building her Hollywood career and didn’t need or want Trump’s attention.
She’s spoken about how he tried to set her up with friends of his when she rejected him directly.
His persistence made the situation uncomfortable rather than flattering.
Her story added to a pattern of Trump pursuing famous actresses.
Hayek’s honesty about the experience resonated with many women who’ve dealt with men who don’t take no for an answer.
She handled the situation firmly, maintaining her boundaries despite any social pressure to be polite.
12. Emma Watson and Tom Felton
Emma Watson had a serious crush on her Harry Potter co-star Tom Felton during their years filming together.
She’s been open about her feelings for him, but Felton saw her more like a younger sister than a potential girlfriend.
Growing up together on the Potter set created a family-like bond between the cast members.
Felton was a few years older than Watson, and during their teen years, that age gap felt more significant.
He cared about her deeply but not in the romantic way she hoped.
Watson has spoken fondly about the experience despite the unrequited feelings.
Both actors remained close friends long after the films ended.
Their relationship shows that not all crushes turn into romance, but they can evolve into meaningful friendships instead.
13. Leonardo DiCaprio and Gisele Bündchen
After dating for several years, Gisele Bündchen decided to end her relationship with Leonardo DiCaprio.
When he later tried to rekindle things, she’d already moved on and rejected his attempts at reconciliation.
Bündchen had made a conscious decision to change her lifestyle and priorities.
Their breakup was significant in both their lives.
DiCaprio was known for his partying lifestyle, while Bündchen wanted something more stable and mature.
She chose personal growth over going back to what was comfortable but ultimately unfulfilling for her.
Bündchen went on to marry Tom Brady and start a family.
DiCaprio continued his bachelor lifestyle and successful acting career.
Her rejection of his comeback attempt showed strength and clarity about what she wanted from life, even if it meant saying no to a Hollywood superstar.
14. Charlize Theron and Seth MacFarlane
In an unusual twist, Charlize Theron reportedly expressed interest in Seth MacFarlane, but he wasn’t looking for anything romantic at the time.
This role reversal, where the woman makes the first move and gets rejected, isn’t as commonly discussed in Hollywood stories.
MacFarlane was focused on his career creating animated shows and directing films.
Theron is one of Hollywood’s most stunning actresses, but timing and personal readiness matter more than looks.
MacFarlane’s disinterest wasn’t about Theron’s appeal but about his own relationship goals.
The story reminds us that rejection goes both ways regardless of gender.
Even gorgeous, successful actresses hear no sometimes.
Both celebrities handled the situation privately and professionally, continuing their respective careers without public drama.
Sometimes people just aren’t in the right headspace for romance, no matter who’s interested.
15. Taylor Swift and Cory Monteith
Before they became friends, Taylor Swift was reportedly interested in Cory Monteith, but he turned her down romantically.
Monteith was starring on Glee at the time and was already in a relationship with Lea Michele, making Swift’s timing unfortunate.
Swift has written many songs about romantic rejection throughout her career.
While she never confirmed Monteith as the subject of any specific song, fans have speculated about which heartbreaks made it into her music.
The rejection didn’t stop them from developing a genuine friendship later.
Monteith’s tragic death in 2013 saddened everyone who knew him, including Swift.
Their story shows that romantic rejection doesn’t have to mean the end of all connection.
Sometimes the best outcome is a valued friendship rather than a failed romance that could have ruined everything.
16. Ariana Grande and Her Co-Star
Ariana Grande has publicly mentioned being rejected by a celebrity co-star crush early in her career.
She didn’t name the person specifically, keeping their identity private, but she was honest about the experience of workplace rejection in the entertainment industry.
Working closely with attractive, talented people creates natural chemistry sometimes.
Grande was young and navigating both acting and singing careers when this rejection happened.
The unnamed co-star either didn’t feel the same way or had reasons to keep things professional between them.
Grande’s willingness to discuss rejection openly helped her fans feel less alone in their own experiences.
Everyone faces romantic disappointment, even future superstars.
She moved past the rejection and built an incredibly successful music career, proving that one no doesn’t define your worth or future happiness.
17. Selena Gomez and Shia LaBeouf
Selena Gomez admitted that Shia LaBeouf was her childhood celebrity crush, and she tried to get his attention but was rejected.
LaBeouf was already a major star when Gomez was still working her way up through Disney Channel shows.
The age difference and career stages made them incompatible at the time.
Gomez was a young teen with a crush, while LaBeouf was dealing with adult Hollywood pressures and relationships.
He likely didn’t even realize she was interested, or if he did, appropriately kept boundaries with someone much younger.
Gomez laughed about the rejection in later interviews after becoming a massive star herself. She outgrew the crush and went on to date other high-profile celebrities.
The story is sweet rather than sad, showing how childhood celebrity crushes rarely work out but make for entertaining memories later.
18. Keanu Reeves and Winona Ryder
Keanu Reeves once joked about asking Winona Ryder out, but she declined, explaining that she didn’t date co-stars.
Ryder had a personal rule about keeping work and romance separate, which makes sense given how messy Hollywood relationships can become when they end badly.
Reeves and Ryder worked together on multiple films and developed a close friendship.
Her rejection of romantic possibilities helped preserve that friendship over decades.
They’ve remained supportive of each other’s careers without the complications that come from dating and breaking up.
Ryder’s policy about co-stars shows wisdom learned from watching others navigate failed workplace romances.
Reeves respected her boundaries completely, proving his genuine care for her went beyond romantic interest.
Their lasting friendship might not have survived if they’d tried dating and it hadn’t worked out.
19. Courteney Cox and Adam Duritz
Courteney Cox and Adam Duritz from Counting Crows dated briefly in the late 1990s, but Duritz ended things and chose not to pursue the relationship further.
Cox found herself on the receiving end of rejection despite being one of television’s biggest stars at the time on Friends.
Duritz was known for dating several famous women during his band’s peak popularity.
His decision to end things with Cox surprised some people who thought they made a good match.
Relationships between musicians and actors face unique challenges with different schedules and lifestyles.
Cox moved on gracefully, eventually finding love and marriage with David Arquette.
The brief romance with Duritz became a small footnote in both their dating histories.
Sometimes relationships end simply because they’re not meant to continue, regardless of how perfect they might look from the outside.
20. Pete Davidson and Cazzie David
After Pete Davidson and Cazzie David broke up, he reportedly tried to reconcile with her, but she firmly rejected his attempts.
David had already decided to move forward with her life without him, especially after he quickly moved on to date Ariana Grande publicly.
Their breakup was painful and public, with David jumping into a new high-profile relationship almost immediately.
When that relationship with Grande ended, David’s attempt to reconnect with David didn’t work.
She’d already done the hard work of healing and wasn’t interested in going backward.
David wrote about the experience in her book, processing the complicated feelings that come with being someone’s backup plan.
Her rejection of his reconciliation attempt showed self-respect and growth.
Davidson continued his pattern of high-profile relationships while David focused on her writing career and personal development.