When it comes to love, society sets women up for failure. There’s an unspoken timeline—date and get engaged in your early 20s, marry by your late 20s, and have kids by 30. No pressure, right?
The pressures of dating and marriage are what prompted Krista Williams and Lindsey Simcik to launch their now-hit show, Almost 30. Between the two co-hosts, there are numerous lessons on love and loss. Alexa, cue Take Care, by Drake! Millennial content creators have walked through marriages, divorce, and seasons of singleness and being “outside.”
Williams and Simcik sit down for an episode of We Met at ACME to share some of their most transformational lessons on finding love, settling, and, more importantly, finding themselves, which ironically might be the key that is missing.
When it comes to love, though it might seem counterintuitive, stop focusing outward. Stop looking at everyone else’s love stories and society’s timelines—your own unique path is the best adventure of all time.
Simcik recalls the late-night texts she received in her 20s, also known as “booty calls” or “sneaky links.” You know the ones. Yea, don’t answer them. When you answer, you are settling. “I was chasing after the wrong guys and settling for very mediocre behavior. I was partaking in these relationships and affirming that the way they were showing up was okay,” Simcik admits.
When you are outward-focused, you won’t hold boundaries and will inevitably settle for breadcrumbs. Instead, ask for what you need and desire in a relationship. Simick recalls the moment when she decided to commit to herself:.“I was crying on the floor one night after not getting invited out. I got so tired of waiting for someone to choose me, invite me somewhere, or give me the greenlight so I could start living my life,” she explains.
What matters to you in dating will change as you get older. Williams, who is now divorced, met her ex-husband when she was in her early 20s. Looking back, she admits that her requirements have changed significantly since then. Her prerequisites in the good ol’ days were athleticism, swag, and popularity—very surface-level and basic, she admits.
After her divorce, Williams took a year off from dating. She is now focused on meeting guys in person. “I keep my energy open. Every single man I meet, I make eye contact and I’m kind,” she reflects.
Williams’ type has changed since working on herself. “Hotties are usually broke or emotionally immature and narcissists. Now that I am older, I don’t want a hottie, but I want someone I can be with my whole life,” she says.
A breakup might be the wake-up call you need to rediscover yourself. After her divorce, Williams learned a lot about codependency and her tendency to prioritize other people’s comfort over hers. “In relationships, you can really lose yourself. A lot of people stay in mediocre relationships and will suffer in a low-grade pain for the rest of their lives because they are afraid of making the choice to move,” she states.
For the ladies who might feel the pressure to stay in a relationship that isn’t working, walking away can bring a sense of reclaiming your identity. “As women, we are taught that breakups are bad, but it is usually the best decision for most women. They change and transform in really beautiful ways,” Williams says.
Instead of saying sorry to your divorced friends, Williams suggests congratulating them. Welcome to 2025 where women are having divorce parties! “The real G’s are divorced. You learn so much. If you take an opportunity and choose to learn the lesson and do the work, it can be the best thing,” she adds.
A profound shift must happen to go from desperately needing someone to choose you to choosing yourself. If you want to stop settling for breadcrumbs in love and dating, it starts with getting to know yourself—your values, your must-haves, and your standards. Simcik is big on “the sacredness of singleness” and taking time to get to know yourself. Do the work, and heal your wounds.
For more dating advice, check out Williams and Simcik’s book Almost 30.
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