Date vs Interview: Strategies for Building Emotional Connections That Make an Impression

How to get out of work mode and into a positively charged date with great conversation.

You Can Date Better
10 min readMay 21, 2023

How do I stop dates from feeling like interviews? This question is thrilling for me to tackle because it begs the question — what’s the difference?

Interviews start off with a power dynamic. Someone is being hired and someone is doing the hiring. The decision making power is initially in one party’s hands to offer and the other’s to accept. Interviews tend to measure skills, experience, problem solving, creativity, teamwork and personability, many times comparing them to other potential candidates and weighing strengths and weaknesses against each other.

This doesn’t sound all too different from dating in some ways, and I’ll admit that many things we do to make a date better will actually make an interview better as well (to some degree). But there are some crucial differences between interviews and dates, and sometimes it’s hard to switch gears and lean in to the difference.

Whether you’re the person that keeps feeling like you’re being interviewed on a date or you have a habit of playing an overly zealous HR team, it’s great to look at how to loosen up and make a date emotionally charged and memorable for both of you.

The True Mission

Dates are all about building emotional connection. When you do that, you will automatically be making a date memorable and special, even if you don’t end up together.

I work with a lot of high achievers that are very mission focused when it comes to dating. Like many things they take on, sitting in front of another person to determine compatibility is a task they want to tackle with all their smarts and efficiencies. Ask all the questions, measure all the responses, find all the flaws, avoid any missteps. Unfortunately, this can sometimes translate to dates feeling calculating, cold, judgmental and boring. Potential candidates are put through a sharply devised scheme of critical conversation with a polite, sterile quality to the meeting.

If a date senses you’re disappointed in them within the first five minutes, you’re not in good date territory. You can decide if they are right for your life after the date, but during your time together, dates are not about passing a test. They are about building rapport as best you can. That takes openness and curiosity, without judgment in the moment.

As much as it makes sense to ask questions to understand someone, coming in with an agenda and rating responses in the moment is a surefire way to kill curiosity and potential chemistry. As soon as someone feels like their answers are being measured instead of being engaged with from genuine interest, the date is dead. You might as well send them a thank-you-for-applying email afterwards. And very likely, no one will ever be good enough to get “hired”.

Similarly, asking basic questions and expecting the other person to be interesting and do all the heavy lifting is a disservice to sharpening your own conversation skill set. You don’t get to sit there and recite the top 30 questions to ask on dates from Google and feel you’ve done your job.

The questions on a date should lead you to having fun, and falling into topics that engage you in new discussion where you have commonalities. You want positivity. You want trust. You want discovery.

So, how do we do that?


One major difference with a date is that you get to shed the work persona, get vulnerable, and talk about things that might be better not to discuss at work. You’re not hiring each other, or maintaining a safe and culturally correct work space. You’re looking for friendship, romance, commitment and respect on the deepest levels. As long as your date is enthusiastically giving you the green light, yes, you can talk about sex. Yes, you can talk about politics. Yes, you can talk about religion.

There is a line early on, but you’re absolutely allowed to voice personal opinions and express how you truly feel about things. You get to show all your sides. This is essential for understanding compatibility on an intimate level — something you don’t need at work.

Vulnerability is a brave and scary thing to do. It lets someone take a peak at potential weaknesses and exposes them to personal information that could feel precarious in the wrong hands.

Remember that your future partner should make you feel safe with that information. Start small (no need to dump a bunch of emotional baggage on date one) but open up a little bit about your personal life on a date and answer questions with authenticity. Vulnerability creates trust — a really great ingredient to partnership.

Speaking of trust, the other beautiful thing about vulnerability is that it encourages vulnerability back the other way. When you both feel you’ve shared some personal intimacy, it creates an emotional bonding moment. That is dating gold, my friends.

One thing to keep in mind if you plan to try being more vulnerable than you’ve been before — be prepared for a variety of responses. For example, a date might be asked about his or her military experience and that answer might not always look or feel good. How we react to vulnerable information is important too. Err on the side of compassion, understanding and curiosity. If someone wants to move on from a topic, follow their lead.


Stories engage our empathy pathways in extraordinary ways and allow us to see other perspectives. Stories provide context to complicated opinions. And stories are way more entertaining to listen to than a polite, canned response to maintain pleasantness.

When we tell stories on dates, we are using the people in our life as characters and showing dates our sense of humor, how we interact with our world, and what’s important to us. For example, a simple, “How was your day?” could be answered with, “Fine, how was yours?” or it could be answered with, “It was kinda boring for the most part, but at our lunch break, my co-worker Sam treated everyone to his homemade cookies and I decided I need to learn how to bake. Do you bake at all?”

We learn so much more about this person with a simple little story. The trick is that it’s short, begs some curiosity, and leads to new discussion naturally. If you feel like you tend to talk too much and tell long stories, make sure the date feels like there is even conversation on both sides and you ask questions back.

Not everyone is an expert storyteller, so they may need some prompting to get through it. Open-ended questions are a beautiful tool for this. Ask the “what” and “why” questions, or questions about how someone feels about something. Ask for a description of a person or situation — what something is like. Relate something they said to a situation or person in your life and then ask another question about their story. Avoid yes/no questions or one word answers.

The short of it: When someone asks a boring question, you do not have to have a boring answer! This can take some practice, but remember that what seems insignificant and boring to your life might be super interesting for a new person to hear about. They don’t know the dynamics of your personal relationships, your work, your passions, your routines. Give them some juicy plot lines to get captivated by!


The pivot is essential for getting out of topics that are starting to get uncomfortable or launching out of a boring, repetitive topics. It’s not that talking about the weather, asking about someone’s day or wondering how long someone has been in their city is a bad thing. It’s just that we’ve all heard those questions so many times that we go into auto-pilot and lose the specialness of this person and this date. You want to stand out.

Did you notice the previous answer to, “How was your day?” suddenly turned into a conversation about baking? That’s a pivot. If a topic isn’t especially compelling for you, touch on it briefly and then move the conversation to a new topic with a short story or a question.

There is no rule about staying on topic on dates. You have the power to direct the conversation wherever it needs to go. I always tell clients, stay specific and current. Talk about what you’re reading, watching or listening to lately and see if you can find something in common there. Come into a date with what’s fresh on your mind and bring it up as if you’ve known each other longer than a minute. That friendly conversation will break the ice and make the other person lower their guard immediately. Trust that your date can jump in and offer a real contribution like a friend would and see what happens. It’s a great challenge!

Unlike interviews where answering the question might be a little more important, most folks don’t care too much if you actually answer their very boring or unknowingly sensitive question. They are just trying to make conversation and build rapport. Pivoting topics is also a great tool if someone asks a seemingly innocuous question that has a loaded answer and you’re not ready to approach it quite yet. Vulnerability has its limits, especially on a first date.

For example, a date asking about your family might bring up things they weren’t expecting. Maybe your mother’s death isn’t something you want to get into on a first date — that’s okay. If you touch on it with a quick heartfelt comment and move topics, your date can follow you. A simple, “She’s passed actually, but my brother is in Arizona with his three kids and they’re a riot. Last week, my one nephew sent me this hilarious video and I realized I’m not ready for them to be teenagers yet.”

Notice when your date is pivoting as well and follow their lead. It’s a simple suggestive tool for moving topics and can take some practice to both implement and learn how to follow it. If the response was that their mother had passed, you can follow the pivot with a simple, “Sorry about your mom, I’m sure that’s tough. Your brother’s family sounds amazing, how old are the boys?” You’ve acknowledged and followed the pivot. When in doubt, pivot again.

Activity Dates

Maybe one of the best ways to get out of a date feeling like an interview is to avoid the sit-down Q&A session altogether! Doing something physical or playing a game at some point on the date can really break up the conversation tension, especially after a first date if you’ve already gone through that experiment. Try finding a spot that has a game you both enjoy, mini-golf, bowling, axe throwing, a farmer’s market to walk around together — anything that gets you both interacting with the world in a different way than just sitting down, face-to-face and talking to each other. Break it up!

Additionally, for those in any job where they might be taking on a bit of a social burden of some sort, spending their free time with another stranger might feel like it’s draining from that same social capital piggy bank, and they’re spent. It’s easy to default to work mode. So get out of the work-like setting!


Hey, guess what? Dating is totally about flirting! That’s something you definitely don’t get to do at work and should probably avoid on all interviews. The big caveat here is about consent — warm eye contact is not going to make a date uncomfortable hopefully, but touching them or trying to kiss them without receiving welcome signals back is a no-no, so remember that consent and communication (both verbal and non-verbal) matter a lot here.

Flirting can certainly build emotional connection and break us out of interview mode, even in its simplest form. Eye contact, laughing, smiling and feeling a hand on a shoulder for just a moment is enough to make a date really memorable and emotional.

I think a lot of folks are nervous about this territory because they want to remain respectful and don’t know where their date’s boundaries are for making physical moves. Good! Yes, you should be thinking about that.

I won’t get into the art of flirting since that’s a whole book, but you can always start small and see what the reactions are to gauge interest. Also, use your words to communicate interest, ask permission and get consent. The point is, dating is a safe place to test and understand romantic boundaries, whereas an interview is an absolutely terrible place for that.

Remember that video dates can be full of flirting too! I had my first two dates on video with my significant other and there was a lot of flirting that had nothing to do with touch, but it built up an emotional connection that made date three feel very emotionally charged from the start. Even on video, get your flirt on!

Saying Goodbye

Unlike the typical interview language of, “We’ll get back to you,” followed by a nerve-wracking waiting game, a better way to end a date is with authentic language around how you’re feeling, and what you want next. If you’re interested and had a great time — say it! Express that you want to see someone again and ask them to text or call you within a short time frame if they’re interested too. Better yet, suggest a second date right then and there.

My advice is to never play games and lead by example. Don’t say you want to go out again if you don’t mean it, and never wait days to text someone you’re interested in because some bogus, outdated dating guide book told you to. Emotional manipulation is out, authenticity and confidence is in. Say how you feel, ask the other person, and make a plan to follow through.

After all that vulnerable storytelling, pivoting, mini-golf and flirting you’ve put out there, the last thing to leave your date with is the respect of a proper goodbye, either with gratitude and closure, or the anticipation of more.

Change the way you date. Get a coach. Get dating.

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You Can Date Better

Writing/content curation by Carrie Prince, founder & boss lady behind — coaching & consulting for the current online dating landscape.