first date conversations

First Date Conversations: Prevent Heartache by Exploring these 5 Essential Topics

Feeling confident to bring up these 5 important first date conversation topics will ensure you have the best first date. If you have the courage and the self-assuredness to take your initial conversations into these essential areas, you can know that what happens next is for your highest good. 

If these first date conversations mean you don’t have a second date, that’s a good thing. A Very Good Thing. If you do have a second date, you can rest assured that you’ve set a good foundation and that you’re not walking into a potential, or more honestly a likely, field of heartache. 

But don’t you want to get to a second date? Maybe. Yet, why go on a second date when you aren’t actually a fit for each other. Dating singles make this biggest of mistakes all too often. They avoid being truly authentic. They avoid asking the questions and exploring these first date conversation topics because they’re afraid of losing their chance with this person. But again, why would you want a chance with someone who can’t meet you in the way you desire to be met? This kind of avoidance and playing it safe isn’t so safe. It leads you down a direct path to heartache. 

Exploring romantic love means that we must risk heartache, but we do not need to put our heart in harm’s way. The best way to hurt ourselves, our heart, and the other person is to turn a blind eye to the ways we don’t fit. 


The purpose of first date conversations

Some people suggest that the first date should focus on fun. While yes, the first date can absolutely include fun, it’s not the purpose of a first date. The purpose of a first date is to determine if you have compatibility in the most important areas. The first date lets you get to know each other and find the common ground, or lack thereof, that suggests whether you have a good fit in the future, based on what you each desire long term. 

If you ignore this information in the beginning it will hurt more when the truth finally comes out. It doesn’t matter how attractive your date is, how exciting their life is, or how kind they are, if your core needs, desires, dreams, and values don’t line up, the potential for long term happiness drops dramatically. 

The risk of not being a fit is well worth the vulnerability of having these conversations sooner rather than later. 

Of course, let the timing of these first date conversation topics flow naturally. Under ideal circumstances, you’d explore some of these questions before your first date so you can find out if dating each other even makes sense.. And, if your first date happens to be an activity that truly makes it difficult to talk, then simply have these conversations as soon as possible. Delaying doesn’t serve anyone and genuine flow matters too. 

You, of course, can’t know ultimate long term fit on the first date or even the first few dates, but you can explore the topics that reveal potential relationship deal breakers. Seek to find out if the two of you meet each other’s must haves. See if you have the possibility of heart and soul alignment in the way you desire it at this time. 

By the way, the more alignment you have, the more fun you’ll have with these first date conversations, no matter what you find yourself doing on the date.


Great conversations to have on a first date

These topics, broken down into 5 essential areas of life, will tell you what you need to know to decide if you truly want to invest in a second date. 

Know that you don’t need to ask every one of these questions, but if you’re looking for first date long conversations, these topics will support you well. It definitely does not need to, and shouldn’t, feel like an interview or an interrogation. Let the conversation flow naturally and if it doesn’t that’s worth noting too. To make things easier, before you meet, you might even consider sharing with your prospective date that it feels loving and kind for you if the first time together would allow space for you both to genuinely explore whether you are a real potential fit for each other.

Topic #1: Relationship Desires 

One of the most important things you’ll want to know about each other is whether you are dating for the same reasons. Some people are looking for their soulmate and want to get married. Some are truly just looking for friendship or companionship. Others seek hook-ups. Still others are just trying to get out of the pain of loneliness or of a recent breakup. And, others don’t really know why they are dating. Make sure your reasons for dating align. 

  • Why are you dating?
  • What kind of a relationship are you looking for?
  • Do you desire commitment? Marriage?
  • What are the qualities of your ideal relationship? 
  • What are your must haves in a partner and in a relationship?
  • What are your deal breakers in a partner and in a relationship?

Topic #2: Relationship Readiness

Depending on your own desires for a relationship and your own reasons for dating, you may care whether your date has the capacity to actually start and commit to a relationship. If you truly seek a long term partnership, a marriage, or a family then, if you want to spend your time well and avoid unneeded heartache, you’ll want to find out if this person is ready for a relationship.

Consider thoughtfully whether you want to date someone who just got out of a relationship, who is separated but still going through a divorce, still living with an ex, or who doesn’t actually know if they are truly ready to be dating. Additionally, their ability to work through and complete with conflict, both past and present, is a powerful indicator of their “longevity” potential. 

You might even want to know if they have brought a conscious ending to their last relationship and prepared themselves for you. If they haven’t resolved and released the painful emotions from their last relationship(s) then you’ll be the one handling their baggage. 

There is no right or wrong in this, but too many gloss over these important distinctions and live to regret it later. 

  • When did your last relationship end? The one before that?
  • Why did it/they end?
  • What’s your relationship like with your ex(s)?
  • Do you feel truly ready to be dating?
  • If you found the ideal partner, do you feel completely ready to make a commitment? Ready to propose, or accept a proposal, even, give the right person?
  • How do you feel about and approach conflict in a relationship?

Topic #3 : Life stages 

You can absolutely have a quality relationship with someone significantly different in age or in a different stage of life. With that, being at different life stages can also make a long term relationship more challenging to create and sustain happily. 

Again, these first date conversation topics empower you to choose consciously. Going into a new potential relationship with your eyes wide open to potential differences will help you clearly know whether you want to keep moving forward. Some of these questions will apply more to you depending on your own life stage.

  • Do you have kids? How old are they?
  • Do you work? What is your work life like?
  • How do you spend your evenings? Weekends?
  • Are you pursuing your passions?
  • What feels incomplete for you in life?
  • What’s next for you on your life’s journey?
  • Do you think about retiring?
  • How active are you?
  • Are you on a consciousness or spiritual path? What has it been like?

Topic #4: Lifestyle and Pleasures

While the topic of lifestyle can feel superficial, again, if you truly desire a long term partnership then having compatible lifestyles, or lifestyles that could easily become compatible, matters. Sharing similar pleasures in life also contributes to our sustainability in relationship.

  • What are your favorite things to spend your time doing?
  • What are your favorite things to spend money on?
  • What are your favorite restaurants? Which ones do you frequent most?
  • Tell me about your most recent vacations…
  • What puts a smile on your face?
  • What is your ideal way to spend a weekend?
  • How much time off do you have?
  • What part of town do you live in? What’s your home like?
  • Does your career put demands or limitations on you?
  • How do you feel about masculine and feminine energy dynamics?

Again, many can feel guilty asking these lifestyle questions. Yet, if we deny our own desires in hopes that we will find a fit, inevitably one or both of you will feel disappointed, inadequate, and eventually resentful. These feelings, if not tended to, will destroy anything you have tried to build together. 

Topic #5: Biggest Dreams

Here’s where the most fun may come in. Ask questions that invite your date to connect with their soul. Our biggest dreams and desires, because they are rooted in our soul, will light us up. And, that light is very attractive. That doesn’t mean you should ignore the other answers you got to the above questions. Yet, this is one of the interesting first date conversations that may truly connect you. You might invite your date to drop all imagined limitations as they answer these questions.  

  • What lights you up most?
  • What’s your ideal life?
  • If you could have anything you wanted in the world, what would it be?
  • If you could live anywhere in the world, where would it be and why?
  • If you never had to make money again, how would you spend your time?
  • If you could give away a million dollars who would you give it to and why?
  • If you could be transported anywhere in the world at this moment, where would you be?
  • What do you most want for the world?

You never know what miracles might bestow you, regardless of current circumstances. Does your date’s descriptions of their ideal life turn you on, light you up, or do they make you go “hmm…” It’s important to just notice.  


Conversations not to have on a first date

If you are seeking true compatibility indicators, do not talk about sex on the first date. Yes, the topic can be edgy, fun and even vulnerable, but it can also give you a “false positive” so to speak. While sexual attraction and compatibility matter, having sexual chemistry and not having the compatibility indicated by the other essential first date conversation topics doesn’t set the foundation for a great relationship. It can set the foundation for trouble and heartache as a matter of fact.

If you have compatibility in the other essential areas, then you can see if there is sexual attraction. Honestly, if you have found connection and bonding through these other first date conversation topics, you will already know if there is physical attraction.

Seriously, save the sexual conversations for later so they don’t distract you. They are a sure fire way to shut down the wisdom of your “picker” and create regrets because the hormones took over too soon. Your heart will thank you later. 


How to listen to and process the answers you receive

You want to be a good conversationalist and you want to pay attention to you. Most importantly, as you explore these first date conversation topics, you want to pay attention to how you feel emotionally. Stay attuned to your natural unfiltered body responses. Notice what happens to your energy as you talk, and as you listen. How do you feel during and after the date?

If something triggers you — either positively or negatively – you could have a soul connection. Triggers can also mean that an old emotional pattern has been activated. 

Pay attention to whether your conversations inspired you to run old unhealthy relationship patterns. Or notice if you projected the past (your ex) onto this date when in reality they are showing up quite differently than your past partner. Were you trying to ensure they didn’t do or like the things you didn’t appreciate or like in your ex? 

If there were a lot of triggers you might want to ask yourself, am I ready for a relationship?

On the other hand, some of your responses might not make logical sense but would serve you to pay attention to them. For example, it could be that your inner knowing knows better than any outer appearance or expression. If you have a “negative” gut feeling, it’s important to trust your intuition. As long as you have checked in with yourself that your date isn’t simply inviting you to expand your comfort zone, as a true soul mate will, then you will likely be best served to trust yourself and skip a second date.


Other things you might notice during these first date conversations

Because the questions above were open ended, you may have learned a lot about your date’s values. You might have also discovered things about their political, religious or spiritual beliefs. 

Here are a few other important things to take note of when evaluating a potential second date.  

You’ll know if… 

  • They’re comfortable talking about themselves…
  • They’re a good listener… 
  • They actually want to know about you – the real you…
  • They are willing to be uncomfortable – an essential part of a lasting relationship…
  • They can be vulnerable…
  • They go deep or stay on the surface… 
  • You feel comfortable/relaxed in their presence…
  • You have a sense of trust in their answers…
  • Any of your spidey senses go off…

The first date and beyond… 

If you’ve asked yourself, or googled, what are good first date conversations? You’ve done yourself a great service. Take the chance to open up these important topics for both of you. Be real and ask your date to be real too. 

If the answers you give and receive during these first date conversations reveal the two of you have a lot in common, awesome. If they reveal you have some significant misalignments, awesome. This data allows you to make good choices that care for you and your heart. Authentically having these first date conversations is actually an act of love, and self love.

Do not try to force fit a relationship. Ask the important questions. Truly listen for the answers. Be open to hearing what you don’t want to hear. Reflect after your date on how the answers you heard and your experience during these first date conversations made you feel. From there decide whether you want to join them on a second date. Your heart will thank you for this approach to conscious dating


Since 2006, highly conscious men and women, with a commitment to extraordinary relationships, have chosen Ecstatic Intimacy to find and cultivate Soul Partnerships from their bedrooms to their boardrooms. Ecstatic Intimacy believes in coveted relationships, for all. 

You too, are invited…

*At Ecstatic Intimacy, an all-inclusive website for singles and couples, we welcome all sexual orientation(s), gender(s) and relationship expressions. In this article we utilize the pronouns he/she/him/her.

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