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How to Know if You Should Go On a Second Date

We all know what kind of date we’d like to have — it instantly feels like you’ve known each other for decades, you talk and laugh all night, and agree you have to see each other again as soon as possible. You know as soon as you close your door behind you that you’ve found your person, and everything will be fine from here on out.

Of course, most of our dates aren’t like this — maybe never. Most of our dates are basically fine; we think the other person is nice, and they think the same of us; we have some interesting points of conversation and some awkward pauses. Maybe we kiss goodnight; maybe we politely hug. When we close the door behind us after getting home, we’re not instinctively sure what our next steps are.

On the one hand, if we didn’t feel an instant overwhelming connection, is it a sign we shouldn’t bother? On the other hand, if they meet enough of the basic things we’re looking for, shouldn’t we give it a second chance, and see if the spark develops? Did we like them, or are they just a nice person? It can feel paralyzing to try to figure out what you even want. You aren’t alone; it can be hard to figure out whether something is worth taking the next steps on. Here’s what I recommend asking yourself when deciding if you want a second date.

Did you have a good time — or did you not have a bad time?

Especially if we’ve been in the dating scene for a while, it can skew our perceptions. We can leave a date feeling like “that went well!” when what we really mean is “that wasn’t as bad as other dates I’ve been on.” It can be genuinely difficult to parse the difference.

What moments of pleasure or joy did you experience during your time together? Are there specific instances you’re looking back on fondly or feel butterflies about? When did you laugh or blush — authentically, and not just to offer a response to your date? If you can come up with several examples — not just things that seem intellectually like a good sign — that’s something to be aware of.

Do you find yourself wanting to continue the conversation?

Thinking about the conversation you had with your new date, it’s okay if it didn’t always flow seamlessly or if you had some hiccups. But are you finding yourself thinking about continuing it? Finding the link to the news article you mentioned and sending it to them to explain what you meant? Did you remember another experimental jazz artist you wanted to recommend but couldn’t think of in the moment? Did you watch the latest episode of that show and want to hear what they think of it?

In practice, a relationship is really just a conversation you agree to have indefinitely; a “successful” long-term relationship is a conversation that goes on forever. Someone that you can talk easily with — and whose thoughts and opinions you want to keep hearing — is a great indicator of real potential.

Does this person have any of your must-haves? Any of your dealbreakers?

Although it’s great to find an immediate spark or chemistry with someone, our romance-obsessed culture can give us the impression that it’s the only thing that matters (which is how many of us end up with people who aren’t compatible with us over and over again!). If you’re having trouble deciding whether someone is genuinely a good fit or just someone more or less nice, a good way to keep your goals for a relationship in sight is to keep your list of must-haves in relationships and dealbreakers.

Making a list of green flags and red flags is a good start; you can choose three of those to become non-negotiables or signs someone isn’t right. Returning to that list and looking at where a new date falls on it can help cut through the dreamy haze of chemical attraction – or let you know that someone is worth a shot even if you don’t feel that right away.

What might future time with this person look like?

We don’t need to start planning our whole lives with someone after meeting them once — but you can start thinking about what it might look like to date them further. Do you have shared interests you could plan dates around? (Or interests that aren’t shared, but you’d like to try — do you want your pool shark date to teach you how to play?)

How would this person fit into your circle of friends? Will they want to go clubbing every weekend while you stay in and perfect your sourdough loaf? How would that feel to you? Does their communication style so far feel like a natural fit with yours? If not, is that an area that could be productive to grow and try new things in? It’s worth thinking through what an even partially shared life could look like; notice where there are natural overlaps or fits and where there might be some friction.

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