When I talk to women my age about their high school dating experiences, almost all of us can recall a time where an older man made us uncomfortable. It could have been a teacher, family friend, older siblings of our friends, or an upperclassman. Almost every woman I talk to can recall a relationship or experience that felt flattering or exciting at the time, but in retrospect the interaction was perhaps inappropriate. We shrug it off. It happens all the time. There is a desensitizing socialization that takes place that teaches young girls to not only accept advances from older men, but to see them as flattering and as a signifier of our own desirability and maturity.

Recently, Canadian rapper Drake has come under fire for his friendship with 14-year-old Stranger Things star, Millie Bobby Brown. Drake, 31, supposedly has a mentoring friendship with the young actress and gives her advice on boys, fame, and life in general. So far there has been no indication that their relationship extends beyond innocent “I miss you” texts and advice on boys, but when Brown’s celebrity status is removed from the equation I am left wondering if it is truly appropriate for a 31-year-old to be texting “I miss you” to someone who hasn’t even fully gone through puberty yet.

Drake would hardly be the first celebrity to form a relationship with someone who is scandalously young. Playful texting and life advice pales next to 35-year-old former Kardashian trophy husband Scott Disick, and his salacious romantic relationship with 19-year-old model Sofia Richie. Disick and Richie came out publicly about their relationship just a few months after Richie took to Twitter defending their “friendship.” During this time, Disick was also spotted by paparazzi being physical with 19-year-old actress Bella Thorne.

Kylie Jenner’s relationship with rapper Tyga, 26, began when he performed at her sister Kendall’s 16th birthday, when Kylie was just 14. As with Drake and Disick, Tyga and Jenner claimed to “just be friends” until Jenner’s 17th birthday, nearly three years later.

Rapper R. Kelly began his relationship with Aaliyah when she was just 12-years-old and he was 24. Aaliyah was the niece of Kelly’s manager and the pair began a secretive “friendship.” Aaliyah came out with her hit single “Age Ain’t Nothing But A Number” soon after meeting Kelly. The two maintained that their relationship was purely friendship until an illegal marriage certificate from 1994 surfaced, which claimed Aaliyah was 18 at the time of the ceremony, when she was actually 15 years old. The marriage was later annulled by Aaliyah’s parents.

Perhaps just as scandalous as R. Kelly’s teenage bride, comedian Jerry Seinfeld began dating his ex-girlfriend Shoshanna Lonstein in 1993, when Lonstein was 17 and Seinfeld was 38 years old. Somewhat unbelievably, this illicit relationship seemed to have little to no effect on Seinfeld’s international comedic acclaim or on the popularity of his sitcom.

This example of a nearly 40-year-old Seinfeld and his high-school-aged girlfriend is rather extreme, yes. So is the example of R. Kelly and his secret marriage to child star Aaliyah, but these relationships hold one common thread with the so-called “innocent” friendship between Drake and Millie Bobby Brown: they started with a friendship and the adamant denial of anything more sinister.

The grooming of underage girls to accept the advances of older men often looks harmless. In most cases it is not as obviously jarring as a 38-year-old Jerry Seinfeld taking his high-school-aged girlfriend out to dinner in Manhattan. It can also look like your friend in his late twenties that repeatedly hooks up with 18- or 19-year-old girls after buying them drinks all night. It’s not about celebrity status. It’s about using flattery and prestige to prey on naivete and insecurity, something which we’re all capable of.

What all of these scenarios share is that the men in question all held some kind of inherent authority or position of prestige which the women were meant to value and seek out. R. Kelly began as Aaliyah’s mentor; Jerry Seinfeld was a highly successful sitcom star; Scott Disick was a reality TV star whose recent divorce from Kourtney Kardashian covered the pages of every tabloid.

Teenage girls should absolutely have the autonomy to make their own choices, but when you’re in dramatically different life stages and levels of independence, there’s an automatic power imbalance that is inherently problematic. When I was a teenager, all I wanted to do was be seen as an adult and to escape the label of immaturity that the word “teenager” carried. I had been taught, from films, television, magazines and my own internalized misogyny that being deemed different from my fellow teenage girls was a good thing and that an older man taking interest in me meant that I had somehow demonstrated exceptional emotional and physical maturity. Seeking out this approval and validation can prove incredibly dangerous when young women are not given the kind of consent-based sexual education to understand healthy relationships.

An implication of these ‘case-studies’ is that all relationships with an age gap are inherently abusive. I know many people who have loving, supportive partnerships with a significant age gap, but these are not the relationships I am concerned with. We need be critical of potential power imbalances and recognize when attraction to younger women go beyond “preferences” and becomes something more sinister. Jerry Seinfeld has enjoyed a decades long career without facing significant backlash for his four-year long relationship with a high schooler. R. Kelly continues to perform and gain traction, despite rumours of his continued abuse of young women. Scott Disick continues to enjoy fame and wealth as the result of his celebrity status. Just because Drake isn’t the first man to do this does not mean there isn’t something very wrong here. Normalizing this behaviour in media only serves to put more girls at risk in our own social circles.