Theo Von Used to Have Trouble Dating — About His Nervousness around Women

American stand-up comedian Theo Von knows a thing or two about relationships. He can be seen giving away dating tips and relationships advice through his podcast, This Past Weekend.

However, the Von we know now was not always the same. In fact, he had trouble making girlfriends and dating women because of his insecurities and nervousness.

Theo Von's Issue with Dating Women

Von opened up about his past struggle to strike conversations with women during an episode of This Past Weekend podcast in September 2021. "I remember when I was young, I could not talk to girls. I just felt embarrassed," he began his video. He shared talking to a girl he liked was the most challenging part of his struggle. 

"I was just afraid," he reasoned, sharing that he used to pre-determine they hated him. The famed comedian walked down memory lane, recounting how hard it was to converse with a girl. The closest thing he could do for a conversation was to throw cringe pickup lines.

"You know I'm a polar bear, I'm about to break the ice," he would randomly say to the girl he liked. Then, he clarified he wasn't comfortable talking to women or asking them out.

The discomfort led to nervousness, and he just felt less of himself, as if he wasn't worthy of someone suitable for him. 

Thankfully, Von got a grip on his issue with low self-esteem and worked out on the part. He started practicing talking to people and realized he wasn't always needed to further the talk. Instead, he could listen to the person and understand them.

After sharing his past struggles, Von requested his followers not to procrastinate and even told them to be picky about finding a girlfriend.

You don't want to end up with someone who doesn't deserve you just because you're afraid to feel like someone does deserve you. 

The Road Rules actor also urged his followers to find comfort, practice listening, and talk about little things initially, even if it meant talking about candies. 

Who Is Theo Von's Girlfriend?

Von has been in many relationships. However, in a 2018 episode of his podcast, he shared he wanted a hard-working, independent, understanding, and funny person as his girlfriend. In his own words, he longed for a woman who dreamt of being a mother and a loving family.

Besides being candid about the qualities he sought in his ideal girlfriend, the 41-year-old also disclosed his past relationships.

He shared he once dated a girl from New Orleans and referred to her as one of the prettiest girls from the city. He described his other girlfriend as the real-life Pocahontas, revealing she was a native American.

Although he dished on tidbits about his ex-girlfriends, Von didn't disclose their identity. That being said, Von was once romantically linked to fellow television star Brandi Glanville.

He and the Real Housewives of Beverly Hills alum reportedly started dating in 2016, after the pair met for his podcast, Allegedly. They even flirted through tweets before they reunited for Glanville's podcast and finally went on their first date.

The relationship, however, didn't last for long. Since the split, Von has not been vocal about his current relationship, although he talks about his experiences. As for Glanville, she briefly dated billionaire Donald "DJ" Friese in 2017.