To help keep the conversation flowing, here are a few ideas for what to talk about during this first encounter. When you first arrive on the date, try starting with a little bit of casual conversation drawing from the context you’re in. For example, if your date picked the restaurant you’re at, ask her if she’s been here before, how she discovered the place, and what she likes about it. Or if you’re at a bar that specializes in quirky cocktails, ask him questions about his go-to drink and share your own. You could also talk about the part of town you’re in and how much time you each have spent in the area, an interesting article of clothing or jewelry your date has on, or where they came from prior to meeting up with you. From there, let the conversation flow naturally—maybe they’ll bring up how hard it is to find good Thai places in the city you’re in, or a good friend who brought them to this spot before, or how much they love eating outdoors. Pay attention to what comes up, ask follow-up questions, and offer up your own thoughts or stories that relate back to what your date just shared. Some people refer to this category of conversation as “small talk,” but the key to making it feel vibrant and interesting is actually engaging with what the other person is sharing and leaning into any opportunities for you both to start disclosing unique details about yourselves. These initial disclosures and early rapport-building will oil up the gears so that the following conversation will feel much easier and more natural. One of the reasons first dates can feel so awkward is that the conversation can sometimes feel like an interview, with each person taking turns asking the other the basic get-to-know-you questions. To open the door to true connection and get past the canned responses, it helps to try to learn about their world as they’re experiencing it presently. Asking about what’s going on in their life currently is a great way to tap into that. However they respond, even if it’s just an exasperated sigh and brief comment about how stressful work is, ask a follow-up question that lets them know that you actually want to hear more about it. Example questions: “When you meet someone, whether it’s in a romantic context or a work context or anything, and you feel how at ease they are with themselves, that makes you feel good. That makes you want to open up, whether you realize it or not,” she recently told mbg. “That’s when we’re like, this is a nice interaction. This is a nice conversation.” “People generally open up more when they’re being seen, heard, noticed, and listened to in the little details of who they are and how they express themselves,” couples’ therapist Alicia Muñoz, LPC, recently told mbg. “Notice someone’s jewelry, the logo on their T-shirt, their overall energy level, their sense of humor, their way of expressing themselves, and celebrate that,” Muñoz recommends. “It’s boilerplate to talk about work, so if you’re going to go there, you might as well take it a step further,” relationship coach Julie Nguyen tells mbg. “What excites them about their job? What doesn’t excite them about their career? What are their dreams for the future? What did they want to be as a kid? By approaching them with curiosity, you can transform simple questions into deep discussions where you draw out the essence of who they are as a person instead of a rehearsed answer.” Example questions: Be mindful entering this part of the conversation: You might end up talking about how isolation and Zoom fatigue have affected your mental health, or you might end up in a politically tinged conversation about how people have or haven’t responded to living through a pandemic. If it ends up being the latter, don’t worry—people sometimes feel like they need to avoid talking politics on a first date, but the truth is that it’s better to know sooner rather than later whether the two of you are aligned in terms of values and viewpoints. Any differences that come up may or may not be a deal-breaker for each of you, but either way, those are important details to know about someone you’re considering dating. Example questions: Example questions: Although common wisdom holds that you should never talk politics or religion on a first date, the days of trying to politely paper over differences for a date are behind us. A 2021 study by the dating app Bumble found that 62% of adults believe it’s important to talk about key social issues on a first date, including topics like gender equality, race, the environment, and more, and 75% said they’d only date someone if most of their political and social views aligned. The truth is, if you’re looking for a long-term partner, shared values are going to be an important bedrock for your relationship—so the sooner you can learn where a potential partner stands on the issues that matter to you, the better. That isn’t to say that you should spend a first date grilling each other about their stances on every political topic, but don’t feel the need to beat around the bush when it comes to your values either. That said, there are a few things you may want to avoid talking about on a first date, such as: Share the things that are exciting, important, and interesting to you, and ask questions to help your date do the same. And remember: Dates should be fun! Focus on enjoying yourself, authentically getting to know this person and allowing them to get to know you, and just having a fun, connective experience together. With her warm, playful approach to coaching and facilitation, Kelly creates refreshingly candid spaces for processing and healing challenges around dating, sexuality, identity, body image, and relationships. She’s particularly enthusiastic about helping softhearted women get re-energized around the dating experience and find joy in the process of connecting with others. She believes relationships should be easy—and that, with room for self-reflection and the right toolkit, they can be. You can stay in the loop about her latest programs, gatherings, and other projects through her newsletter: kellygonsalves.com/newsletter
