What I learned from going on 230 dates with EAs

Published on October 5, 2026 2:30 PM GMT A conflict of interest to flag: I'm the founder of Settled, a relationship and matchmaking company with free and paid tiers.  That may create bias in what I notice and what I recommend, so weigh these recommendations accordingly.  I’d love for some of you to sign up to Settled, but my aim here is to share something useful whether or not you ever do.   What this post is and isn’t  We’re writing this because we hope it provide helpful insights - people have also asked, so here it is! This post is based on: Hundreds of hours of interviews and coaching  with 350+ singles Data from Settled: nearly 2K completed questionnaires & hundreds of feedback forms from dates we set up An ongoing literature review (with help from Claude) - 70+ papers reviewed Our insights are observational, there's no control group and we collected all data for the purpose of setting up good dates, not research or analysis. We're including it because operational data from inside a matchmaking service is rare, not because it's complete or correct.  Some observations and learnings from building Settled  1. Dating apps are problematic; you should probably still use them There are a variety of known problematic dynamics associated with dating apps, ie: Apps waste a lot of time: we’ve talked to daters who spend tens of hours per week on the apps, and end up without quality dates App use is associated with worse mental health: two 2026 meta-analyses (Cela & Wood 2026; Sharabi et al. 2026) find small-to-moderate associations with worse depression, anxiety, loneliness, and behavioural dysregulation. Although it's important to note that these studies are cross-sectional and compare users to non-users, which is confounded by the users being single. Apps can increase unhelpful dating behavior: larger choice sets make daters more rejecting (acceptance falls ~27–29% across a session, Pronk & Denissen 2020), shift them onto cheap cues like height and weight (Lenton & Francesconi 2010), and produce less-satisfying, more reversible choices (D'Angelo & Toma 2017) Apps are incentivized to keep you single and on the app as noted on a recent post from Clearer Thinking: And despite this, dating apps are still a common way that couples meet today.  A massive number of single people are on dating apps, so they're your biggest pool of potential matches. They are also good if you have broad preferences, or if a specialised app (ex. Feeld, Coffee Meets Bagel, ChristianMingle) narrows down your pool of preferences.  If it does make sense for you to keep using the apps, here’s some tips:  Use the apps alongside alternatives, ie: events, introductions through friends, communities you're in for their own sake, and matchmaking. Limit your use by limiting session frequency or length, and cap time when sending messages – just send it! Whilst Hinge and  Bumble tend to have the biggest pools, some apps that are built to avoid some of the dynamics listed above, two examples we know of: https://breeze.social/ (also has an EA aligned founder!) but worth noting it’s not in every region https://www.compassmeet.com/ Move to meeting quickly. Finkel et al. found that extended pre-meeting communication builds expectations that the actual person then has to survive. A long text rapport is not evidence of anything. 2. Just ask questions and be on time. People overthink first dates enormously. Whether the joke landed. Whether the outfit was wrong. Whether they should have picked somewhere else. If they should have offered to pay instead of split, or criticizing why they fell short of producing the single best insight on planet earth. We ask both people for feedback after every date we set up, including what the other person could have done differently, and here’s what it tells us: 54% of responses contained no improvement suggestion at all. The modal answer was some version of “no notes, they should just be themselves” Among the responses that did suggest something, the most common themes we saw are: ~20% Ask more questions, show curiosity, balance the conversational airtime (often mentioned by women as their biggest complaint) ~11% Logistics: be on time, don’t end abruptly for because you take the date between engagements, etc So, yeah: be yourself, ask questions, and be on time. 3. We’re bad at knowing how the first date went.  If you've ever set two friends up and then spoken to both of them afterwards, you'll know how this goes: they describe two different evenings. That's not unusual, it's the normal case. Reading a stranger accurately, while also managing your own nerves and performance, is genuinely hard. We see this phenomena at scale: we ask both daters for feedback after every date.  One question we ask is, “How interested did they seem in you?” on a 1-5 scale. Here’s how it pans out: Of the people who thought the other person was interested in them (rated 4-5), that person was not open to seeing them again 25% of the tim