Dating is hard. And not just in a mildly frustrating way—in an emotionally exhausting, soul-numbing, why-am-I-doing-this-to-myself type of way. I truly enjoy being single and value my independence, but I’d be lying if I said I didn’t still crave that whirlwind romance. You know, the kind of all-consuming soul connections that you read about in books and watch on-screen. But unfortunately, that kind of romance just isn’t always the reality. Where’s the yearning? Am I the problem? After countless dead-end conversations and more than a few truly awful first dates, I wondered what, if anything, I could be doing differently.
In the pursuit of making my dating life a little bit better, I decided to turn to the experts for help. I spoke with Dr. Sabrina Romanoff, a psychologist and relationship expert at Hily Dating App, to gain more clarity and even a little hope. What she gave me was a thoughtful list of eight dating rules. These “rules” aren’t harsh, though—they’re more like practical mindset shifts that challenge the way we approach dating. From her perspective, by changing our approach, we’re more likely to find meaningful connections. So if you’re feeling burnt out, discouraged, or just ready for a different kind of dating experience like me, these dating rules are for you.
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Dr. Sabrina Romanoff, PsyD
Dr. Sabrina Romanoff, PsyD, is a relationship expert at Hily Dating App and a Harvard-trained clinical psychologist. Based in New York City, she specializes in helping individuals and couples navigate anxiety, trauma, and the complexities of modern dating. Her work focuses on building healthier connections, managing relationship stress, and fostering more fulfilling romantic lives.
1. Focus on how the relationship makes you feel
It’s so easy to get wrapped up in checking all the boxes of a partner that sometimes we forget to pay attention to what really matters: how that person actually makes us feel. Instead of obsessing over a long list of traits like job, height, or eye color (finance, trust fund, 6’5″, blue eyes, ring a bell?), Dr. Romanoff recommends taking notice of your emotional and physical experience around them. Do you feel confident, secure, energized, and mentally stimulated? Notice your reactions from the very first text, during the date, and in the moments after. Tuning into these signals over time helps you gauge your true emotional compatibility beyond what looks good on paper. “Make a tangible list of how you want to feel in their presence, and assess whether you are able to feel this way after interactions,” says Romanoff.
2. Measure relationship progress by how you connect, not what you achieve
Romanoff says that a lot of people focus on hitting the big milestones like becoming official, meeting friends and family, moving in together, or getting engaged. But those aren’t the only things that matter. Some of the most important goals in a relationship are much more than your “stereotypical” relationship markers. “For example, it could be to express vulnerability and comfort each other, initiating intimidating conversations around money, family planning, and future goals,” says Romanoff. These kinds of goals help both you and the relationship grow, keep the focus on what you can actually control, and build confidence and trust as you date. Maybe it’s opening up more, or initiating a conversation that feels scary or uncomfortable. Pay attention to how that conversation unfolds—how they respond, whether they offer support, and if they share their own vulnerability. That’s often where the real progress happens.
3. Be flexible where you can and firm where it matters
The hallmark of any strong and healthy relationship is compromise—but it’s also important to know where you draw the line. While there are some things you can be flexible with, others might be an absolute dealbreaker for you. This means having confidence in your boundaries and staying grounded and self-aware. “Don’t get swept up in the honeymoon phase and overlook real incompatibilities,” says Romanoff. When you’re clear on your non-negotiable values, dating gets way easier (and way less frustrating), because you’re not trying to bend yourself—or someone else—into something they’re not. Romanoff recommends, “Write down your top three non-negotiables (wanting kids, authenticity, emotional responsiveness) and check in after each date to see if they’re able to embody them, rather than being directed by chemistry or momentum.”
4. Reflect on yourself as much as you reflect on potential partners
Obviously, a big part of dating is getting to know someone on a deeper level. However, people often forget that being in any kind of relationship is also a great way to learn about yourself. Whether it’s your relationship habits, triggers, or past traumas—all of that comes to the surface when you’re being vulnerable with another person that you care about. As Romanoff puts it, “The real work is noticing when those things get activated and choosing a response that actually serves you—like stepping back from emotionally unavailable people instead of chasing them.”
One helpful habit that Romanoff recommends is reflecting after each date: What came up for you? Did anything trigger insecurity, jealousy, or anxiety? Maybe you noticed a reaction when they mentioned an ex. Paying attention to these moments helps you understand how past experiences may be shaping your current dating behavior, allowing you to respond more intentionally.
“When you’re clear on your non-negotiable values, dating gets way easier, because you’re not trying to bend yourself—or someone else—into something they’re not.”
5. Build a community while you seek out a potential partner
Dating is hard enough as it is—you shouldn’t go it alone as well. You need people in your corner to vent to, laugh with, cry with, and help you see things more clearly when your judgment gets a little cloudy. That support might come from friends, family, or even a therapist. Romanoff recommends that we “Choose one safe, reliable, and steady person to regularly debrief dating experiences with.” Having a go-to person you can be fully honest with makes it easier to talk through concerns, reality-check your thoughts, process your emotions, and stay grounded in what you actually want—especially when you start to get a little blinded by your feelings. Not to mention, forming real, honest, and supportive connections outside of romance helps broaden your sense of where joy and fulfillment can come from.
6. Let conflict reveal compatibility
Disagreements are a part of any relationship—romantic, friendship, or family. We can all agree on that. But what matters most is how you both handle them. While it can be as silly as an argument about a movie or restaurant, these little clashes show how you both deal with frustration, negotiate differences, and manage tension. Do they communicate calmly, listen to your side, or brush things under the rug? Do you feel heard or dismissed?
Noticing how you both navigate small disagreements gives you a sneak peek at how bigger, more serious conflicts might play out down the line. “Pay very special attention to how they take responsibility for hurting you, their ability to listen to your perspective, and actively take steps to repair the relationship,” says Romanoff. Their patterns don’t have to be a total dealbreaker, but they give you important information about how you might work together in a relationship.
7. Choose growth in real time, over the potential of who they could be in the future
We’ve all heard it (or thought it ourselves): “I can change him!” It’s so easy to fall for the idea of who someone might become instead of paying attention to who they actually are right now. Potential is tempting, but growth is what really matters. True growth shows through real, tangible ways. That doesn’t mean just saying “I’m sorry,” but actually showing it through actions: being thoughtful, listening, owning mistakes, and showing empathy. Romanoff suggests asking yourself a tough but important question: “If this person never changed, could I genuinely be happy in this relationship forever? Could I handle the messy, complicated parts of life with them—kids, money, family, and everything else?” Their current behavior is the clearest clue for what life with them will actually look like—and it’s better to know that now than to learn it the hard way later.
8. Pay attention to lifestyle compatibility, not just chemistry
It’s easy to get swept up in love and ignore red flags. When you’re caught in the honeymoon phase, you might focus only on how they make you feel and overlook whether your lifestyles, routines, or priorities actually fit together. Chemistry is great, but it can’t carry a relationship on its own. Long-term compatibility is about the everyday stuff too: whether you’re a morning or night person, how your schedules line up, energy levels, social habits, health routines, and even family dynamics.
Romanoff agrees that couples can thrive despite differences, but doing so requires communication, consideration, and thoughtfulness. “This means compromising, making room for each other’s needs, and recognizing that what supports your partner’s wellbeing may differ from your own,” says Romanoff. She recommends checking compatibility by imagining a typical week together. Do your schedules overlap, or are they constantly clashing? Will you both be able to get your needs met without one person constantly giving up what’s important to them? Paying attention to these small, practical rhythms early on can save a lot of frustration later—and it gives a clearer picture of what life with them will actually look like.
Jenna Piotrowicz, Editorial Assistant
Jenna began working as an Editorial Assistant for The Everygirl in 2024. With her eye for detail, she assists the team with content creation, sourcing products and images, and works behind the scenes to support The Everygirl in uploading and updating content.
