Estimated reading time: 12 minutes

After being single for far too long and finding the apps to be all but useless, I’ve started going to events and mixers that are specifically for dating. Many of these have been speed-dating events or had a speed-dating component, while others have had various mechanics or setups that are supposed to keep everyone mingling and talking to many people over the course of the event.

The problem is that I’m not a great conversationalist with someone I don’t know. It takes time until I get to know someone for conversation to be easier because I know enough about them to really get into it. Paradoxically it was always easier on dating apps where I at least had something in their profile to start the conversation. In person, I find myself falling back on boring interview questions like their job, how long they’ve lived here, any siblings/family and so on. It won’t surprise you that I rarely get matches from these events, and I feel certain that I’m not connecting with people well.

How do I talk to a complete stranger in a dating-specific context? What do I talk about when we may have a grand total of 5 minutes to decide if we like each other or not?

Too Much To Say Not Enough Time To Say It

Given the option, I find that a more generalized mixer – one that encourages participation, conversation and meeting many people but isn’t structured like speed dating – to be a better option overall, but they can have their own issues as well.

As a general rule, the key to connecting with people and getting them to like you is to focus on how you make them feel. The more you can affect people on an emotional level, the more likely they are to want to spend time with you. When you’re at an event where time is of the essence, like speed-dating, then the key is to skip the getting to know you questions and instead focus on standing out by being fun and interesting to talk to.

Most of the conversation that people have at speed dating events tend to be banal, and it makes it easy for each person to blur and blend with the others until very few stand out. Focusing on topics that will not only elicit an emotional response but are actually engaging helps not only capture the person’s attention, but also their interest. So rather than asking who someone is or what they do for a living, I would recommend starting with something along the lines of “what’s something you’re very passionate about?”, “what’s the most absurd hill that you’re willing to die on?”, or “What did you want to be when you grew up?”  These are questions that get to the heart of who a person is, rather than a recitation of basic biographical info that ultimately tells us very little. They show an interest in what’s important or meaningful to the other person and invites them to open up more than those standard interview questions do.

Just as importantly though: very few people ask questions like this and they lead to far more entertaining and interesting discussions than just talking about work.

You might also look at some of the posts on social media that are open-ended engagement bait for examples of questions that capture people’s interest right away. “Would your 20-year-old self be impressed or disappointed by you today?” got over 3000 replies on Bluesky alone. Other questions like “What’s the most random fact that you know?” also can serve as a springboard for an immediate conversation topic that is going to be far more interesting than comparing jobs and asking about how long they’ve lived here.

This can admittedly be tricky; we’re used to starting with those low-stakes questions to establish a baseline before we get into the more meaningful topics. Skipping them feels like we’re breaking some rule of etiquette, and it’s easy to end up going on autopilot without realizing it. Breaking the rule, such as it is, requires intent and being deliberate in how we approach the situation.

It also requires having the confidence to encourage the other person to play along – many people can be surprised at first when they get a non-standard question and may not have an answer right to hand. It helps to have your own answer locked, cocked and ready to rock, so that when someone says “well, what do you mean?”, you can reply with “My most absurd hill is that snack foods peaked in the 90s with the PB Crisp, and everything since has just been trying to iterate on what came before instead of coming up with anything new or good.”

What you don’t want to do is to ask questions that can be answered with one or two words, or that don’t lead into a conversation. Anything that can be answered with just a number, a “yes” or “no” or that is otherwise not open-ended tends to shut down conversation rather than promoting it. So if you aregoing to ask biographical questions, ask about their feelings about things rather than facts. How they like living in the city, what they enjoy about their job, what their experiences have been like with $INSERT_SUBJECT_HERE all give more opportunities for exploration and more questions, rather than just rote answers.

You also want to pay attention to your body language and the overall impression that you’re giving to the other person. What you want is to project focused warmth, interest and attention – making the other person feel like you think they’re the most interesting person in the room and you are prepared to listen to their life’s story. A warm, genuine smile, relaxed and open body language, even leaning forward a bit while they talk helps convey that you’re pleased to see them and you’re interested in what they have to say.

And if you want something a little sneaky, you can even give a little surprised-but-pleased “wow…” when you sit down – a little “accidental” gesture that says that you weren’t expecting someone that cool, interesting or attractive when you came to this event.

Incidentally, this works well in non-speed-dating contexts as well. While you don’t want to necessarily skip the small talk when you’re meeting someone for the first time when you’re not constrained by time, focusing on interesting questions that ask people about things that are important or meaningful to them and encourage them to share about themselves makes you more interesting in the process. And as I’ve said before: showing that you’re impressed by them, rather than trying to impress them, goes a long way to help you stand out from a crowd that mostly is waiting for their turn to speak, rather than showing actual interest.

Good luck.

How many chances are we supposed to give someone if we’re trying to decide if we like them or not? I’ve moved to a new city for work and I’ve been trying to get established by meeting new people and going on dates. Since I don’t know the city that well yet, I’ve been mostly focusing on meeting people through dating apps like Hinge and Bumble and I’ve had a decent amount of success at meeting people.

The problem I’ve been having is that I’m frequently meeting people where there doesn’t seem to be much of a spark or interest, either on my side or theirs. When I’ve talked to friends of mine about this, they’ve all suggested that I should give people more of a chance if I’m just lukewarm on them. If they don’t have any serious red flags and I’m not actively repulsed by them, so my friends tell me, I should consider at least giving them another date or two before I decide to write them off for good. One friend compared it to how she gives a new tv series three or four episodes to find its footing before she commits or bails on it.

I will be honest: I’m not sure how I feel about this. While none of the people I’ve met have been awful, more often than not I’ve been neutral on them. They seem nice enough, but after we say our goodbyes, I’m not concerned with whether I’m going to see them again and so I tend to leave it at that. Am I missing out by expecting instant chemistry and sparks from my matches? Should I be giving people more of a chance to grow on me if I think they’re ok but not exciting? And does that go both ways? While there have been a couple people I wouldn’t have minded seeing again, they didn’t seem interested that interested in me; should I be reaching out to them in the same spirit of giving a couple of tries before we decide?

Third Time Lucky

I’m of two minds on this, TTL. On the one hand, I think that one of the recurring issues in modern dating is the expectation that there’s either an immediate and powerful connection or it’s time to move on. A lot of relationships are born when they’re given an opportunity to grow and breathe, rather than expecting it to be like lightning from out of the blue. While powerful chemistry from the start can be exciting, it’s also an incredibly unreliable indicator of whether a person is actually a good match for you. It’s also not the norm; most of the time we don’t start relationships with someone we just met, nor do we fall in love at first sight.

On the other hand, I also don’t think that there’s any benefit to trying to force attraction when it’s simply not there. While there’s a lot to be said for giving room for something to blossom, sometimes you’re trying to water a dead plant.

So my not terribly helpful answer is: “it depends”. While this isn’t satisfying, I know, the issue is that it really is going to be dependent on the person and the situation. Dating apps, for example, not only encourage that “immediate chemistry” expectation, but also create a number of false positives in our matches. Much of what dictates who we are or aren’t attracted to can only be determined in person. No matter how well written the profile is, how good the photos are or even how great the chemistry may be when you’re messaging back and forth, you still can’t guarantee that you and your match have the necessary x-factor that makes the difference between feeling neutral about someone and being wild about them.

But just as importantly, there’s the question of whether you want to see the other person again or not. It doesn’t do anybody any good to ask for – or accept an invitation to – a second date if you’re pretty sure this isn’t for you. The overall goal of dating – and online dating in particular – is to spend as little time with people who simply aren’t right for you while trying to find the person or people who are. If you’re accepting or offering another date out of a sense of obligation rather than interest, then you’re ultimately wasting each other’s time. Especially if one of you is interested and the other person isn’t; that’s time that the interested party could have given to finding someone who likes them back, instead of hoping to make a rose bloom in a desert.

My overall suggestion would be to take things on a case-by-case basis and consider why you felt the way you felt after the date. There’s a difference, for example, between a lack of interest and a date that was working against the two of you. Sometimes what can make the difference between a mediocre date and an amazing one is the venue or the activity; how we feel about a person is often influenced by how much we enjoyed the date itself. If the date was at a loud and raucus bar, for example, you might have a hard time really feeling like you got to know them – especially if you (or your date) aren’t someone who likes loud bars. Similarly, if there were outside issues – poor service at the venue, inclement weather, people being jerks bringing down the mood, even unexpected allergy attacks – then the issue was often the date itself and not the company. In a circumstance like that, it might not be the worst idea to take a mulligan and try again… but plan for something completely different this time.

You might also ask yourself whether you were genuinely uninterested, or if it’s a case of “They’re neat, but it wasn’t fireworks and cartoon cherubs when we met”. If, for example, they seem like they’re kind of cool or interesting, then it may be worth your time to see if that grows into more over the course of the next date. It may well not; they may confirm that they’re nice but not quite what you’re looking for. Or you may discover that while they’re not what you’re looking for in a romantic or sexual partner, they may be a good platonic connection.

Alternately, you might give someone a chance if it seems like there was potential, but the other person was struggling for some reason. If the other person was nervous or having a bad day, for example, they might not be coming to the date at their best. If you feel like there’s a chance where you both may have a better time on date 2, then by all means, give them that opportunity to make a better first impression.

On the other hand, if you know for a fact that this is just someone who’s not your particular flavor of “yum” for whatever reason, then it’s better to shake hands and wish them the best of luck in their search, rather than to give false hope.  

However, one thing I would suggest is that when you’re meeting people off dating apps, your first date should be more of a vibe check than a date. I’m a proponent of what I call a pre-date date, where you arrange to meet up for 15-20 minutes or so for coffee, ice cream or something similar and just see if you mesh as well in person as you did on the apps. These should be in person, not just over Zoom or Facetime; you’re looking for those subtle signs of compatibility that can only be determined in person. If the two of you vibe well enough on the vibe check, then you can plan a second and more “traditional” date and see how it goes. If you don’t… well, then the worst that happens is that you’ve only lost around 20 minutes and the price of a latte.

Good luck.