Are Deep Conversation Starters Really Necessary?

Are you sick of all the failed relationships you’ve been through in the past? Do you feel tired about going through the dating stage all over again just to discover he’s not worth it?

They say that great conversation starters spark a deeper connection with a person, and asking him a series of questions can help you clarify things for the future.

You want to know if he’s dating anyone else. You want to know if he’s open to commitment. You want to know if he’s the man of your dreams. You want to cut to the chase and save yourself the pain effort of dating by asking him direct questions – just so you can feel secure. 

No one judges you for being concerned about your future, or even wanting to ask a few leading questions to determine whether he’s husband material. 

But is a deep conversation starter necessary in the dating stage? Do you really need to have a meaningful conversation at your first meeting to tell that he’s the one?

Conversation Starters that Can Help

It’s fine to ask some meaningful questions to your date as a means of starting a juicy conversation. They could theoretically open up an interesting half-hour discussion that reveals something useful. So, to have the same conversations – “What do you do? Where do you live? Are you close with your family?”, you can consider the following conversation starters. :

  • What makes you happy?
  • What matters most in your life?
  • What do you find attractive in others?
  • How do you want people to remember you?
  • What’s your favorite family tradition?
  • What makes your day perfect?
  • What’s the craziest thing you’ve ever done?
  • What are your future goals?

These simple questions will provide insights into a person’s interests, attitude, and background. 

However, I wouldn’t suggest you approach each new date like a journalist. Using a few funny conversation starters might keep things interesting, but dating has to be more natural. If you happen to have deep conversations, that’s fine, but you don’t want to interrogate your man because he’s probably not going to enjoy it very much.

Dating Shouldn’t Be a Q&A Interview

It’s normal to feel curious and try to ask probing questions to your potential partner. But dating shouldn’t be a Q&A interview. Here’s why:

Using deep conversation starters can be counterproductive.

It’s not that you’re “wrong” for wanting to learn more about the other person, his views on dating, relationships, sex, communication, commitment, money, religion, and politics.

It’s that it’s “ineffective” to interview men for the part of “husband.”

A central metaphor of my Love U program is that women are the CEOs and men are the interns applying for a job, but that’s not literally true. He’s 50% of the equation, and if you want to see him again, you need to get him to like you. And what makes men respond to you is how he feels on a date. Are you warm, curious, enthusiastic, and flirtatious? Or do your questions make him feel like he’s at the police precinct, and your only assumption is that he’s guilty?

First impressions go a long way, so put more emphasis on making him feel attractive and interesting than on your fear of wasting time on the wrong men. 

And remember: love is full of surprises. Unexpected conversation makes dating more exciting.

Intimacy takes time to grow.

Intimacy takes a lot of time to grow. You can watch its progression over months, years, and even decades. So while I can understand your desire to want it all upfront, the level of intimacy that makes for a solid relationship foundation probably won’t occur on those first few dates. 

It’s common for a woman who deeply desires a romantic connection to confuse chemistry with intimacy. Chemistry is great conversation, sparks flying, and the anticipation of a next date. Intimacy is closer to compatibility, where you’re fully known and accepted. 

Don’t mistake one for the other.

For example, you can have long hours of serious talk with a stranger on an airplane, but that doesn’t imply that you’ll get along well in real life. It only means that you and he just let it all hang out because you’ll never see each other again. 

This is not to suggest that all conversation should be shallow or that true connection is impossible, but from what I’ve seen, people assign too much meaning to going deep early on. 

The getting-to-know-you part is crucial.

Is it possible that he’s just like your ex? Is it possible that he’s just a waste of time? After all, you don’t want to end up with the wrong person. You don’t want to spend time with someone who’ll abandon you. You want to ensure that you don’t get hurt.

This is all understandable. 

However, you can’t take a shortcut to know your future. If you do that, you might just end up putting too much pressure on him and ruining your chance of finding a lifetime partner.

Remember, he has as much at stake as you do. He doesn’t want to waste time or get hurt either. But neither you nor he has any idea what the future holds. In Love U, we talk about “not trying to read the last page of the book,” and that metaphor holds true. All you can do is slowly turn the pages together and discover what comes next. You can’t get ahead of a story that has yet to be written. 

Getting asked a series of deep conversation questions can be stressful, especially on a first date. Once you’re in a relationship, he’ll be more comfortable sharing more of himself and his flaws because he knows you can accept him – and he can accept you.

When Is the Proper Time To Have a Serious Talk?

You want to cut the small talk. You want to ask about things like religion, having children, past experiences, financial responsibilities, sex, and more.

You might be in a hurry because you just want to settle in a stable relationship. It’s true that you don’t have all the time in the world, but still, it’s important to keep things flowing naturally and listen intently to the person talking.

The art of conversation shouldn’t feel more like a tennis match than an interview. Topics are volleyed back and forth organically, not because you have a list of questions you need answered, but because, in spending time together, subjects naturally arose.

A man who wants to get married will talk about getting married. A man who wants kids will talk about wanting kids. A man who is passionate about his ambitions will mention his career.

In other words, you don’t need to have a great conversation starter just to pry things out of him. You just have to spend some quality time and listen. If a man never mentions something you deem important, chances are, it’s not that important to him. 

Wait for him to open-up

Waiting for him to bring things up and talk about what you want to know might test your patience. But it’s part of the process and a crucial one. If he’s willing to commit to you, he’ll open up about his plans, and you’ll be a part of them. You don’t need an agenda to get to know the real him; you only need openness between the two of you.

It will not be easy, but it’s important to value letting him reveal himself over time rather than pushing him too much out of your fear of making a mistake.