The Nine Essential Questions to Ask on a Date to Future-Proof Your Relationship

In today’s ever-evolving dating landscape, ensuring compatibility and clarity early on has become crucial for singles seeking meaningful connections. Dating app Bumble predicts that in 2025, “future-proofing” relationships will be a major priority, with 95% of singles considering their long-term goals when choosing a partner.

To navigate this terrain, professional relationship counselor Therapy Jeff, known for his insightful TikTok advice, has crafted nine vital questions that every dater should consider asking. These questions are designed to encourage open communication and avoid unpleasant surprises later.

A relationship expert has devised a list of questions for a first date (Getty Stock Images)

1. Does Anyone Else Think They’re in a Relationship with You Right Now?

While it might sound absurd, this question addresses the complexities of modern dating. Between casual flings and undefined “situationships,” ensuring exclusivity is a must.

“You might think you’re single, but someone else might not see it that way.”

2. What’s Your Definition of Cheating – Both Physical and Emotional?

Cheating isn’t universally defined. What feels acceptable to one person might be a deal-breaker for another.

Jeff emphasizes:

“Discuss everything—flirting, liking photos on social media, or consuming explicit content. Define what counts as betrayal for both of you.”

3. What Kind of Relationship Do You Want?

With the rise of diverse relationship structures—monogamous, polyamorous, or open—it’s essential to understand your partner’s expectations.

“Monogamous? Monogamish? Poly? Do you want to open it up in the future? Or is the plan to stay committed exclusively? This sets the foundation for understanding each other’s goals.”

Asking the right questions is important (Getty Stock Images)

4. How Do You Feel About Living Together Eventually?

It might seem intense for a first date, but understanding long-term goals can save time and heartache.

Jeff explains:

“Is cohabiting a goal, or do you prefer something like living apart together? Does moving in mean a trial run, or is it a step toward marriage?”

5. What Kind of Wild Stuff Are You Into in the Bedroom?

Physical compatibility is as important as emotional. Asking about preferences early on avoids surprises later.

Jeff says:

“It’s good to understand expectations, whether it’s something to look forward to or decide if it’s a deal-breaker.”

6. What’s Your Biggest Worry About Us?

Every relationship comes with its challenges, and addressing them upfront can pave the way for smoother communication.

Jeff encourages honesty:

“Put concerns on the table early and see if you can navigate them together. Knowing what might become tricky can build trust.”

Understanding each other's needs is key (Getty Stock Images)

7. Are You Prepared to Be My Primary Emotional Support?

A strong relationship thrives on mutual emotional support. It’s crucial to determine whether your partner is ready to be there for you.

“Understanding how much reassurance or emotional availability your partner can provide is vital for long-term compatibility.”

8. What Are You Giving the Most Energy to Right Now?

This question provides insight into your date’s current priorities and how a relationship might fit into their life.

Jeff explains:

“It could be work, school, family, or creativity. Knowing where their energy goes helps set realistic expectations about your role in their life.”

9. What Do You Think Is Important for Me to Know as We Move Forward Together?

An open-ended question like this invites honesty and introspection. It’s a chance to uncover any hidden truths or critical aspects of their life.

“This often leads to surprisingly honest and insightful answers. Building a relationship without secrets is always the better path forward.”

Why These Questions Matter

First dates are often filled with surface-level conversations. However, addressing deeper topics early on helps singles align their goals and values, avoiding wasted time or mismatched expectations.

As Therapy Jeff highlights, “Future-proofing relationships isn’t about being overly serious—it’s about clarity and connection.”

So, the next time you find yourself swiping or preparing for a first date, consider these questions. They might just help you find someone who’s truly aligned with your vision for the future.

Featured Image Credit: Getty Stock Images