“Why Do My Dates Feel Like Interviews?”

Let’s make sure that your dates don’t feel like interviews…  

Sometimes a date can feel like a job interview, even though nobody wants that. (!)

Have you ever been there? On a date, saying to yourself…

Uh oh, why does this conversation feel like a boring interview right now?

It happens!

Somewhere after comparing and contrasting her preference for Stevia + half-and-half and yours for black coffee, the conversation lost steam (no pun intended). ;)

You definitely feel attracted to her, and she may even be attracted to you by the way she’s glancing down and blushing every now and then…

But all those flying sparks are careening dangerously close to Loss Of Interest Zone (a cousin of the Friend Zone!) if this feeling of a job interview keeps up.


So why do your dates feel like job interviews?

Well, you might be feeling pressure to keep endless questions coming in order to avoid awkward silences.

Problem is, when a date devolves into a question-and-answer session, it’s tempting to just try harder and buckle down at keeping the conversation going.

Since “trying too hard” isn’t a good look, that leads to both you and your date feeling uncomfortable and anxious, rather than relaxed and excited…

And relaxed/excited is definitely the vibe we’re after!

So how do we keep things engaging and fun?

Awesomely, that’s what this post is about.

So let’s get into how to make sure your date conversations flow beautifully!


With the right balance of effort and ease, you can make your dates feel awesome.

When you put in an effort to engage and be present with your date, that is so attractive!

Note: Not feeling very attractive at the moment? We can help! Download our ebook and do the exercise on page 8 to find your uniquely attractive jam.

Effort shows that you are benevolent, that you are using your power for good, and that you are thoughtful.

You can show great effort by… 

  • listening sincerely, which wonderfully shows through your facial expressions and body language
  • responding in kind, and then turning things back to her after awhile with an observation or sincere question.


Those are wonderful.

That said, too much effort can be bad…

While a conversation does take a certain level of engagement to flow; too much effort makes for a stilted, stiff conversation, which is not what we’re going for.

Trying too hard on a date can look like…

  • asking a series of questions that feel so cliche to you that it almost feels like you’re reading them from a list.
  • being over-the-top in your responses, trying hard to impress her.


And guess what?

Your date will feel it when you are asking questions just to say something!

Instead, you want to be engaging her in artful conversation, developing a flow and sense of comfort in the silence, as silences are only as awkward as you make them.

This relaxed engagement gives you time and space to amplify the chemistry flowing between the two of you.


Create flow on a date.

The big-picture framework of conversation is that you and your date are jointly creating an experience of each other.

When you’re interested in a woman, you are experiencing her, and she’s experiencing you.

The experience is amazing because it’s a combination of…

  • your attraction to her,
  • her vibe, and
  • how she comes across.

She’s experiencing you at the same time, feeling…

  • attraction,
  • your vibe, and
  • how you come across.

The two of you are collaborating to create the experience of each other on your date.

Afterwards, with that sweet feeling in the air, you may have forgotten the details of what you talked about, but you’ll both remember the experience.

This is wonderful news because it takes the pressure off.


Talk about what is important and enjoyable to you.

When you’re trying to talk about things that don’t interest you, that’s when fears of being dull, uninteresting, or needy crop up… because feigning interest can feel like all of those things!

The solution is find genuine common ground of values, interests, and experiences.

This helps you feel more relaxed and excited, which naturally sets the tone for y’all’s dynamic and helps bring out the same in her.

Keep in mind that about 7% of what elicits relaxation and excitement from her will be in the actual content of what you say. The rest is in how you feel saying it and how she feels hearing it.

The key is to make sure you feel good about everything you say on a date.

If you don’t feel good about saying it, don’t say it. (!)

A few moments of silence is better than racing to fill the empty spaces saying things you don’t feel good about saying.


Offer possible jumping-off points to her in conversation.

When you talk about something that you’re excited about or that you’ve noticed about her (the cocktail-making class you tried last weekend, the book you’re reading, or the volunteer work she’s doing), you’re giving her something.

You’re adding to the rapport and chemistry between the two of you by sharing genuinely.

You’re also giving her an opportunity to jump off what you’ve just said into the beautiful pool of her own inspirations, ideas, memories, and musings.


By sharing with passion, you’re helping her to do the same.

This is much better than asking her endless questions, hoping she’ll eventually be interested.

If you are only saying things to try and impress her or “make” her say something back, then you’re taking from her, detracting from the chemistry and rapport.

The great thing about a flowing conversation is you don’t have to be clever or witty; you just need to be actually engaged in sharing and listening in a way that feels good for you and therefore can connect with her.

A sincere conversation creates more intrigue, building the tension between you just a little bit more, as you both get excited to know each other more.


Pull from three reliable topic areas on your dates.

There are three primary topic areas to talk about on a date:

  • the Environment,
  • Her, and
  • You.

These three topic areas are perfect because they allow for dynamism in the conversation.

You can flow between these topics pretty naturally without ever racking your brain for something surprising or witty to say.

All you need in order to never run out of things to say is to remember the three base topic areas and get better and better and finding them in different situations.

Pro Tip: In your everyday conversations at the office, with friends, wherever…

Practice seeing that low-hanging “topic fruit”, which means keeping an awareness of what the topic areas are and intentionally noticing them in the moment.


Talk about the Environment

Especially on a first date, you could start with the environment because it’s less personal and vulnerable to begin with.

There’s the micro-environment of the venue where you met her for the date.

You can talk about things like the ambiance of the place, the food, the drinks, the music, even other people you see around you.

Then there is a broader environment of the context of your life and her life, like your communities, places you enjoy visiting in your city or town, and so on.

The topic of the environment often overlaps with the other two topics.

For example, if you’re talking about what running group she enjoys, you’re talking about her local running group environment, and you’re talking about her.

Even though there’s a crossover, when you think of the environment as its own topic, it helps you come up with things to talk about.

To get better at seeing more environment-based topics, the next time you go out, make a concerted effort to notice what’s around you to help stimulate topics about your immediate surroundings.


Talk about Her

To direct the conversation toward her, you can bring up something you’re noticing about her.

Mentioning something you notice about her is direct and can be intense depending on what you say.

You could comment on something she’s wearing, something beautiful about her, something you like about her, or just something you’ve noticed about her.

Don’t be afraid to mention something about her as long as it’s positive, genuine, and respectful.

There are lots to appreciate about that kind of sincere comment.


Talk about You

Talking about you is more vulnerable than talking about the environment, yet less bold than talking about her.

Any topic about yourself can range from greater or lesser degrees of vulnerability.

You can let yourself be more vulnerable as you get more comfortable as the conversation progresses.

For example, you can start with a few basics like something you’re thinking about, something that excites you, something relevant and recent that happened in your life, or something fun and positive that you’re doing these days.


When should you talk about the Environment versus Her versus Yourself?

First, no matter what you say, keep it positive. You don’t want to introduce negativity into the conversation because that’s no one’s best look.

As a solution, here are some positive things you can say in these main topic areas:

Talk about the environment…

  • When you see something around you that interests you.
  • When you’re curious about something in the immediate or broader environment.

Talk about her…

  • When she’s having a strong effect on you. She’ll likely be touched that you were vulnerable enough to tell her that.
  • When you feel curious about something about her.

Talk about yourself…

  • When you think of something that excites or interests you,
  • When she asks you about yourself (of course). ;)


Keep in mind…

There is a lot of overlap between the three topics areas. If she’s having a strong effect on you, and you tell her about it; then now you’re talking about her, and you’re talking about yourself.

When you’re out on a date, know that you can always find conversation topics by going back to the three base topics:

  • The Environment,
  • Her, and
  • You.

If your dates feel like interviews, this will all be quite helpful!

Having these topics, as well as a generous approach to conversation, will help your dates feel like adventures instead of interviews.


Summary on “Why Do My Dates Feel Like Interviews?”

Trying too hard is one of the major reasons why sometimes dates feel like interviews.

The right balance of effort and ease allows for conversations to flow beautifully and helps prevent dates from feeling like job interviews.


Summary of what to talk about so your dates won’t feel like interviews: 

  • Bring up what is important and enjoyable to you.
  • Offer possible jumping-off points to her in conversation.
  • Share with passion, which helps her to do the same.
  • Pull from these three reliable topic areas on your dates: the environment, her, and you.

The important thing to always remember during your conversation: No matter what you say, keep it positive. Don’t introduce negativity into the conversation.


There’s More!

If you need more support to help make sure that your dates don’t feel like job interviews, check out our Launch Your Dating Life program.

Clients who’ve graduated from that feel so much more confidence, ease, and connection with women. We’d love to talk about it with you and see if it’s the right fit for you with your current challenges and goals.

To discuss it with us, please apply at the bottom of this page. 

Sarah Jones
Sarah Jones
Sarah Jones is founder and CEO of Introverted Alpha; the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of Sarah's 22-page ebook inside the blue box just below.

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