Monica Lewinsky's Love Life Hasn't Gotten Any Better Since Her Bill Clinton Affair

The public first heard the name Monica Lewinsky in the late 1990s, as part of a very public scandal that derailed all parts of her life. This included everything from Lewinsky's financial situation to her career aspirations to her ability to leave the house without photographers in tow. A less discussed aspect of Lewinsky's situation has been the effect of the Bill Clinton affair and subsequent scandal on her social life. Though Lewinsky has many strong friendships — including some with famous folks such as Alan Cummings, Chelsea Handler, and Molly Ringwald — she has struggled when it comes to finding a long-lasting romantic partnership.

As her public image has shifted in the last decade thanks to a well-received Vanity Fair essay, a viral "Ted Talk," and evolving cultural discussions about power differentials, slut shaming, and other important topics, Lewinsky has begun to share more about the years she was off the grid. The anti-bullying advocate has also become more open about discussing her love life, both in interviews and on her popular podcast, "Reclaiming with Monica Lewinsky."

Still, don't expect Lewinsky to name any names anytime soon. "I kinda feel if anybody has earned a right to have their romantic life private, it's me," Lewinsky told People in 2021. "Those relationships are very precious to me, even the one or two who turned out to be putzes. But I've learned a lot." Still, we do know a bit about Monica Lewinsky's love life, and all of its challenges, since the Clinton affair.

Dating is hard for most people, and it only gets harder the older one gets. For Monica Lewinsky, there's the added pressure of having intimate parts of your life on display well before you even walk into a room, let alone go on a first date. This makes dating, as Lewinsky says, quite complex, and it has changed the goals she originally had for her personal life. "I have always dated, not always successfully dated," Lewinsky explained on the "Call Her Daddy" podcast. "I was somebody who had wanted to get married and have kids, and I'm sort of past that point of having kids naturally, so I think that was a focus for a long time, but it was definitely, my dating life has been complicated, I think, at times."

There are many reasons why Lewinsky says dating has been complicated, including the fact that she identifies as an "anxious attacher." The star said on Dax Sheppard's podcast, "Armchair Expert," that she needs a lot of reassurance from romantic partners in order to feel secure. Lewinsky has also said that public shaming around her sexuality has made romantic relationships more difficult in some ways. "I think our comfort level, and it might be generational, but I think comfort level of really feeling like you can own your own sexuality fully can be one layer that many of us go through when you add on the way I was sexualized and humiliated around sex," she explained.

There is no debating that Monica Lewinsky is thriving professionally. In addition to her podcast and anti-bullying work, she is also a Vanity Fair contributor and has a production company prepping an Amanda Knox-focused scripted series. While the world is finally seeing Lewinsky for who she is beyond the headlines, she still appears to have her guard up in many ways — and who can blame her? In terms of romance, this has manifested in a deep distrust of dating apps meant to help facilitate interaction. "I'm not on the apps. I am like, 'I can't. I'm going to be catfished. I am so gullible.' I think it's a level of trust that is just not quite there yet," Lewinsky confessed in a 2025 Rolling Stone interview.

Though she has not gained a comfort with dating apps, Lewinsky still dates and has dated for most of her time out of the public eye, often with the help of friends. "It's mainly setups," she said in the Rolling Stone article. "I date, I have relationships, situationships, all the things. I've had connections with some extraordinary men. I've been really lucky. Not lucky enough that it's been with someone where it's worked out at the right time. It just hasn't...I still have lots of issues." Though life may not look the way a young Lewinsky thought it would, she appears hopeful about finding a long-lasting love — and her supporters are equally as excited about the prospect of Lewinsky getting a happy ending.