On TikTok, Kaitlin Reagan Gets Vulnerable About Dating After Loss

In Bustle’s series Shooting Your Shot, single influencers weigh in on drinking and dating: their drinking rules for a first date, drink order ick, and more.

It may come as a surprise to her over 3 million TikTok followers, but Kaitlin Reagan, 26, hasn’t always been an optimist. When you experience rock bottom, though, you have no choice but to change your perspective. “Going through what I have has changed me into the person I am. At your lowest, the only way to look is up,” she tells Bustle.

Reagan joined TikTok in 2020, a story she knows is “just like everybody else’s” but her time on the app has been anything but. She started by occasionally posting random videos that got a few thousand likes, but it wasn’t until a clip of her pranking her boyfriend Francesco Lopresti went viral in March 2020 that followers started rolling in. Then, in March 2022, Lopresti passed away from cancer at age 24.

Prior to his passing, the couple had updated their followers about Lopresti’s health, but Reagan knew she had to take some time away to grieve on her own before coming back to the limelight. “I took a year off to recenter before going back online and asked myself, ‘Who do I want to show back up as when I get back out there?’" she says. “I was pretty open about everything [in my grief journey] except for the fact that I was ready to date earlier than I shared because I was really scared of judgment.”

Naturally, Reagan’s content has evolved since she first started TikTok, but that vulnerability remains. Last month she shared a “Get Ready With Me” video before her first date since Lopresti’s passing. The comments were overwhelmingly positive.

“I tell [my followers], ‘I don't have it all figured out. I'm just like you trying to navigate this new life that I'm creating for myself. Join me for my mistakes. Join me for the things I do right and let's just grow together,’” she says.

Below, Reagan talks about navigating difficult topics on first dates, her pre-date ritual, and the sexiest way to meet someone IRL.

What would you say to someone who thinks they need to lower their standards since the dating pool can be so rough?

If you haven't found what you're looking for, you're not meant to have it right now. I don't think lowering your standards is ever necessary. If anything, it's like the universe telling you, “not right now.” It will come but just give it some time.

Is there a drink order that would give you the ick?

I want somebody that's ordering something exotic. No basic drinks, like a vodka cranberry. Or if you're ordering a tequila seltzer and you don't even know what tequila you're asking for and just getting whatever tequila is on the rack, let's spice it up a little.

How do you prepare for a first date?

I need to take at least a shot or two before going on any dates just to feel a little bit looser.

As someone who has experienced incredible love and loss, how do you decide what is OK to talk about on a first date?

Deep conversations are important to me, especially with everything I've been through. I don't have time to have a surface-level date. I want to sit down and pick somebody's brain and I want them to pick my brain.

I want to ask important questions. Do you have a big family? What's your relationship with them? Have you ever been in a long-term relationship? Because I don't want to waste the person's time. I don't want to go on a second date if it's not realistic and we're not on the same page. If that person isn't able to have those deep talks, then that means it's probably not going to work long-term.

Do you have any advice for people who are nervous about meeting someone out in the wild?

I just think it's so sexy to own if you think somebody's handsome. I would say don't think too much about it, just go for it. Chances are you probably won't see that person again if you're worried about rejection. Just say, "Hi. You caught my eye. Would love to connect in some way,” and see what they say. What do you have to lose?

This interview has been edited and condensed for clarity.