She tells you about a trip she took last year, something she’s genuinely excited to talk about, and instead of asking her more about it, you find yourself already telling her about a bigger trip you took, a more exotic destination, a wilder story from your own travels. Or she mentions a genuinely tough week at work, and before she’s even finished, you’re pivoting to your own tougher week, layering your own struggle right on top of hers. It feels, from the inside, like relating to her. It reads, from her side of the table, like competing with her, and those are two very different experiences even though the underlying impulse can feel similar in the moment.
One-upping is almost always unconscious, and it’s worth understanding where it actually comes from, because most guys who do this aren’t trying to dominate the conversation on purpose. It’s a habit built up over years, often years of social environments where being interesting meant having the better story, the funnier joke, the more impressive credential. In a lot of professional and social contexts, that instinct genuinely serves you well. On a date, it does the opposite, because it quietly communicates that the conversation is actually about you, and her stories are just convenient entry points into your own.
Let’s walk through a concrete example of what this actually sounds like, because it’s a subtle pattern until you hear it laid out. She says, ‘I went to Portugal last spring, it was honestly one of the best trips of my life.’ A one-upping response: ‘Oh nice, I went to Portugal too actually, but I also did Morocco right after, it was insane, let me tell you about this one night in Marrakesh.’ A genuinely engaged response: ‘Oh really, what made it one of the best? Where did you go?’ The difference isn’t subtle once you see it side by side, but it’s genuinely hard to catch yourself doing the first version in real time, because it feels, in the moment, like you’re building rapport through shared experience.
There’s a version of this that’s slightly harder to spot, because it doesn’t even involve a competing story, just competing struggle. She mentions a hard week, and instead of one-upping with a more impressive achievement, the guy one-ups with more suffering: ‘oh that’s rough, my week was even worse, let me tell you.’ This is arguably worse than the achievement version, because it actively takes attention away from someone who was reaching out for a bit of empathy and redirects it toward the listener’s own need for sympathy instead. It’s a subtle but real form of taking rather than giving in that exact moment.
The fix is genuinely simple to describe, though it takes real practice to execute consistently, especially under the mild anxiety of trying to make a good impression. When she finishes a story, stay in it a beat longer than feels natural at first. Ask a specific question about her experience before bringing up anything of your own. Let her story be the center of that portion of the conversation for slightly longer than your instinct wants to allow. You’ll get your turn. The conversation isn’t a scarce resource where every second she has the floor is a second you’re losing.
This connects directly to empathy, one of the four pillars I coach, and it’s worth being specific about why. Genuine empathy means staying with someone else’s experience because it matters to them, not immediately redirecting attention back to your own experience, even if your intention in doing so is genuinely to relate and connect. Redirecting too quickly, however well-intentioned, communicates that your own story takes priority over fully hearing hers, and that message lands regardless of your actual intent behind it.
I want to add a nuance here that’s important, because the goal isn’t complete self-erasure either. Sharing your own related experience isn’t inherently wrong, and total silence about yourself has its own problems, coming across as flat or withholding. The skill is sequencing and proportion. Ask more about her story first, genuinely engage with it, and if a related story of your own comes up naturally afterward, that’s completely fine. The problem isn’t that your story exists. It’s when it arrives too fast, cutting hers short before it’s had room to actually land.
There’s a specific version of one-upping worth calling out separately, because it’s subtler than the travel-story example and shows up constantly in coaching: achievement one-upping around work. She mentions a project she’s proud of, and instead of asking about it, the response becomes an update on a bigger project of his own. This one is especially common among high-achieving, competitive men, because competitiveness that serves them well professionally gets carried unconsciously into a context where it actively works against connection rather than for it.
If you’re someone who notices this pattern in yourself and finds it hard to break in the moment, a useful trick is keeping a mental count during the date, not obsessively, just a loose awareness of how many times you’ve redirected a story of hers back toward yourself. Simply having that number in your head, even roughly, tends to interrupt the automatic pattern enough to catch it before it happens a third or fourth time in a single evening.
Worth remembering too that the payoff for fixing this habit shows up almost immediately, often within the same date. Women consistently describe feeling truly listened to as one of the more rare and memorable qualities in a first date, precisely because so few people actually do it well. It’s a low-effort way to stand out.
When she tells you about her trip to Italy and you jump in with your better trip to Italy, you’re not connecting with her. You’re competing. One-upping usually comes from wanting to seem interesting, but it tells her you were just waiting for your turn to talk. Ask a follow-up question and let her story stay hers, because learning how to actually listen matters far more than having the best stories. It’s a common habit behind why high-achieving men make terrible first impressions, and it’s often a sign of the kind of forced confidence covered in what nobody tells men about confidence.
If you notice this pattern in yourself, and it’s an extremely common one, especially among guys who are naturally good conversationalists and used to holding a room’s attention, it’s worth catching deliberately before it becomes a habit that quietly costs you connections you’d otherwise have made. And when you’re ready to put the fix into practice, my matchmaking partner LEVEL Connections can get you a real shot with someone genuinely worth listening to, fully, without the competition.
