In Bustle's series Shooting Your Shot, single influencers weigh in on drinking and dating: their first date drinking rules, drink order, and more.
This may come as a surprise to her more than 3 million TikTok followers, but Kaitlin Reagan, 26, hasn't always been an optimist. However, when you hit your lowest point, you have no choice but to change your perspective. "Things I've been through have made me who I am today. When you're at your lowest, the only way to do that is to look up," she tells Bustle.
Regan, who joined TikTok in 2020, knew the story was "the same as everyone else's," but her experience on the app was anything but. In the beginning, she occasionally posted random videos that garnered thousands of likes, but it wasn't until March 2020 when a video of her pranking her boyfriend, Francesco Lopresti, went viral that fans began to pour in. Then, in March 2022, Lopresti died. Diagnosed with cancer at age 24.
Prior to his death, the couple updated fans on LoPresti's health, but Regan knew she would have to take some time away to grieve alone before she could return to the spotlight. "I took a year off before getting back online and asked myself, 'Who do I want to be in front of when I get back out there?'" she said. "I've been open about everything [in my grief journey] except the fact that I was ready to date before I shared it because I was really afraid of other people's judgment."
Of course, Reagan's content has changed since she first created TikTok, but the vulnerability remains. Last month, she shared a "Get Ready With Me" video ahead of her first date since LoPresti's death. Reviews are overwhelmingly positive.
"I tell [my followers], 'I haven't quite figured it out yet. I'm just like you, trying to navigate the new life I've created for myself. Join me in correcting my mistakes. Join me in doing what's right, Let’s grow together,” she said.
Below, Regan talks about handling difficult topics on a first date, her pre-date rituals, and the real-life sexiest ways to meet someone.
What would you say to someone who thinks they need to lower their standards because the dating pool can be so rough?
If you haven't found what you're looking for yet, you shouldn't have it right now. I don't think there's a need to lower standards. If anything, the universe is telling you, "Not now." It will come, but give it some time.
Is there a drink that makes you feel sick?
I wanted someone to order something exotic. No basic drinks like cranberry vodka. Or if you're ordering a tequila soda but you don't even know what tequila you're going to get and you're just buying what's on the shelf, let's spice it up a bit.
How do you prepare for a first date?
I need to drink at least once or twice before going on any date, just to feel a little more relaxed.
As someone who has experienced incredible love and loss, how do you decide what 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 for superficial dates. I want to sit down and listen to other people's opinions, and I want them to listen to mine.
I want to ask important questions. Do you have a large family? What is your relationship with them? Have you ever been in a long-term relationship? Because I don't want to waste the other person's time. I don't want to go on a second date if it's not realistic and we don't see eye to eye. If that person can't have those deep conversations, 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 in the wild?
I just think if you think someone is handsome, it's so sexy to have it. What I'm saying is, don't overthink it, just do it. If you're worried about rejection, you may not see that person again. Just say, "Hi. You caught my attention. 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.
