Red Flags In Bettina Anderson And Donald Trump Jr.'s Relationship From Our Matchmaker

The ink has barely dried on the high-profile split between businessman-turned-politico Donald Trump Jr. and outspoken MAGA spokesperson Kimberly Guilfoyle, but they're officially old news. Already, everyone is more focused on Don Jr.'s new flame, Florida socialite Bettina Anderson, and not all of this attention is positive. Mere months into their relationship, many online seem skeptical that Trump Jr. and Anderson are built to last.

According to Mediaite, several sources have accused Anderson of chasing "transactional relationships" and suggested that she's only using the Trump heir as a means to get ahead, possibly even angling for a position on some government committee. Meanwhile, onlookers in Anderson's corner seem similarly (if inversely) puzzled by the match. "Are these women desperate?" commented one Reddit user. Another wrote, "Bettina's friends need to do an intervention."

It looks like audiences on both sides of the aisle have misgivings. But what are Trump Jr. and Anderson's actual chances? To find out, Glam spoke exclusively with Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking. In her professional opinion, there are "so many glaring red flags" that Trump Jr. and Anderson will need to get past if they want to go the distance, from rushing into things to their notable political divides.

In this day and age, most couples don't need a familial blessing to see each other, but it's still nice to have. Sadly, it seems like Bettina Anderson hasn't managed to endear herself to Donald Trump Jr.'s family quite yet. "Donald Trump [Sr.] does not approve of his son's association with Bettina," a source told Mediaite in January 2025. "Bettina's presence is seen as a liability rather than an asset." Another added, "Family members are particularly worried about the optics surrounding Bettina's reputation," referencing Anderson's long-established rep as a party girl.

As Susan Trombetti exclusively tells Glam, this adds up to quite the issue. "She has definitely failed to charm the president. ... When you don't have your dad's approval, it can be a problem. For example, your family may give your love interest the cold shoulder." For example, Anderson was conspicuously absent from the swearing-in ceremony on Inauguration Day, even though she'd shared photos of an "Inauguration glam" outfit in an Instagram story that morning. Neither did she join her paramour at the inaugural lunch, raising speculation that she'd been dissuaded from attending.

To be fair, the Trumps weren't necessarily fans of Don Jr.'s ex, either, despite Kimberly Guilfoyle buying into the "Mar-a-Lago face" aesthetic that they seem to prefer. In 2024, a source told Radar Online, "Despite what the Trumps might say in public, they were never fully behind Kimberly. Some of them were even turned off by her." We've all seen how that story turned out, and it's hard to say whether things will go any better for Anderson. She may need to prove her commitment to the Trumps to get past this red flag. As Trombetti observes, "The family needs to rally some support for the relationship."

Prior to their split, Donald Trump Jr. had been with pundit Kimberly Guilfoyle for almost six years. They'd stuck together through thick, thin, and some of Kimberly Guilfoyle's most inappropriate outfits. However, that long commitment didn't stop Trump Jr. from practically sprinting into Bettina Anderson's arms. "Don Jr. didn't take any time to process what went wrong with Kimberly Guilfoyle before moving on. You always need to do that to ensure success in your next relationship," Susan Trombetti exclusively tells Glam. After all, without examining where things went wrong, how can you avoid the same mistakes in future partnerships?

"It's a bit quick," Trombetti adds, and this is putting it kindly. In actuality, the jumbled timeline between Guilfoyle and Anderson suggests that Trump Jr.'s fast rebound comes with an alleged side of infidelity. Trump Jr. and Anderson were romantically linked in September 2024 after sharing brunch in Palm Beach, Florida — plus a few shamelessly public kisses. As an anonymous source spilled to the Daily Mail, "They were definitely on a date. ... They weren't exactly making out, but the kisses were romantic, and you could tell they were intimate with each other." Another source added, "'I guess they're not trying to hide it. They've been seen together all over Palm Beach."

The problem? Trump Jr. didn't confirm his split from Guilfoyle until that December — months later. "Don Jr. appeared to jump in quickly with his current love interest after ending things with his former fiancee. That makes things awkward," Trombetti observes. In this case, the overlapping timelines aren't a good look for Trump Jr. or his ability to maintain healthy relationships.

Donald Trump Jr. may be earning some side-eye for how quickly — or even prematurely — he leaped from Kimberly Guilfoyle to Bettina Anderson. However, he's not the only one moving fast. For some reason, both Trump Jr. and Anderson seem to be in a hurry to shift their dynamic from casual dating to coupled up. Not only have they been on several romantic getaways together, escaping to locales like Italy and the Bahamas, but the duo are also spending all of their stateside time together. "Don Jr. is essentially living with Bettina at her townhouse," an inside source told Page Six in January 2025, only a month after the couple officially went public with their relationship. "His car is always there. Always."

"They are said to be currently living together, so this relationship moved at warp speed," says Susan Trombetti. Unfortunately, the matchmaker doesn't think this is a good sign for longevity. As she exclusively tells Glam, "This is always problematic. The quicker to sizzle, the faster it fizzles."

True enough, skipping straight to cohabitation is one of the telltale signs that you're rushing into a relationship. To avoid running face-first into this red flag, Anderson and Trump Jr. should probably pump the brakes and get to know each other better before entwining their lives any further. Then again, maybe it's love at first sight. Stranger things have happened. As Trombetti notes, "Time will tell."

Donald Trump Jr. and Bettina Anderson may be enjoying their honeymoon phase, but lifestyle differences are poised to throw some speed bumps into their path. Critically, Anderson's social and political views put her at odds with her boyfriend's fanbase — not to mention his immediate family. "Politically, Bettina, although a Republican, isn't quite on the same political page as this family," points out Susan Trombetti. "She is more bipartisan and stands out for her moderate republican views. She was an advocate for stricter COVID rules and other environmental policies that conflict with President Trump's."

For instance, in November 2020, Anderson shared a Facebook photo promoting COVID safety. In the shot, she wore a face mask and held a sign reading, "Only you can stop the spread of ignorance" — a sentiment contrary to much anti-lockdown MAGA messaging of the era. Anderson is also a known proponent of green causes and the Black Lives Matter (BLM) movement, which are more closely associated with leftist politics than with the Trumps' constituents. "Muted but listening," she wrote on Facebook in June 2020, posting a blank black square in support of BLM's #BlackoutTuesday awareness initiative. And in April of the same year, she posted on Facebook for Earth Day: "The future looks bright, but that is mostly because it will be on fire. ... #ClimateChange."

That's a lot of outspoken opposition to Trump family politics. Usually, political views aren't the end-all-be-all of romantic compatibility, but the Trumps are figureheads of an entire movement — and their opinions get a lot of attention. "Media scrutiny and the public spotlight are always a huge pressure for any couple in their position," Trombetti exclusively tells Glam. And if Trump Jr. and Anderson aren't careful, that pressure could get the better of them.

Among Bettina Anderson's moderate political views, one may hold particular relevance for father-of-five Donald Trump Jr.: her total lack of interest in motherhood and tradwife roles. "Every day is Independence Day when you don't have children," she joked in a Facebook post on July 4, 2020. Even her Instagram profile proudly announces, "I'm just your typical stay-at-home mom...only I don't do household chores...or have a husband...or have kids." This doesn't exactly mesh with a political party that has celebrated derogatory comments about single "cat ladies" and childless women.

More crucially, it could clash with Trump's expectations. Putting aside that several of Anderson's potential in-laws try to bill themselves as all-American housewives, she'll eventually have to contend with his five kids: Kai, Donald III (nicknamed Donny), Tristan, Spencer, and Chloe. Maybe Anderson won't move fully into a stepmom role, even if this relationship takes a turn for the serious. Still, she can't just ignore them.

Getting past this red flag may take some doing. Step one? Toning down the dissonance between Trump Jr.'s conservative views and Anderson's lifestyle. "I think at this point, Bettina needs to not make her politics so known since they can conflict with [Trump Jr.'s] beliefs," Susan Trombetti suggests exclusively to Glam. "It's not to say that she can't have her thoughts and be her own person, but she definitely shouldn't flaunt it. The two of them should keep a low profile. ... Let's see if they can make it as a couple for a bit before being so exposed."