Simon Becchetti

5 Revealing Questions You Need To Ask Your SO Now

When you're in a relationship, it can seem like all you do is talk — about your feelings, about your likes and dislikes, about your future plans.

But at a certain point, the typical couple's talk starts to fall short and leaves you wanting to have deeper conversations about more complex subjects. Unfortunately, these subjects tend to be the hardest ones to bring up.

So, where do you go from here?

Now, we generally wouldn't recommend beating around the bush when it comes to communication, but hear us out on this one: Sometimes the key to tackling tough topics is approaching them from another angle. If you start by posing a random question, your conversation will often go to a deeper place in a totally organic way.

You might be surprised at how much a thoughtful answer to a simple question can reveal about your partner.

So, when you get to the point in your relationship when you have a desire to start talking about the big stuff, don't freak out. Start with easy questions and trust that the big stuff will come out when it's time.

Here are five revealing questions that will reveal a lot about your SO.

1. If you won $50,000, how would you spend it?

Believe it or not, this fun hypothetical can reveal a lot about your SO's mindset. The Discover® and Match Group study — which explores how finances factor into our dating lives — found that most people want to discuss financial topics within the first six months into a relationship. This question is a great, low-pressure way to get that conversation started.

Whether the answer is “quit my job and spend a year traveling” or “invest half and pay off student loans with the other half,” you'll learn exactly what s/he values when it comes to spending a large sum of money.

2. When was the last time you cried?

Get the tissues ready. Just kidding, but seriously: This question is a surefire (albeit slightly awkward) way of gauging how emotionally vulnerable your SO feels with you, and how s/he responds to different tear-jerking life situations.

And if your SO won't admit to shedding a tear, like, ever? RUN, because you're either dating a liar or a robot.

3. If you could snap your fingers and achieve a non-career goal, what would it be?

When you're talking about life goals with your partner, it's easy to stick to work-related milestones like promotions or new jobs.

But specifically asking about non-career-related goals opens the door to discussing the more personal ambitions that are slightly harder to admit to, like self-improvement or paying off debt.

4. What's the most embarrassing thing you've ever spent money on?

Asking about past financial missteps isn't meant to shame your SO — it's meant to get you talking about a subject that can be seriously difficult to bring up in everyday conversation.

Discussing bad money decisions as a couple will give you insight into what your partner has learned from his or her mistakes, and about what plans s/he has in place to avoid similar blunders in the future.

5. What were your past relationships like?

Talking about past relationships (and what may have gone wrong) is crucial when you're dating someone. Yet that doesn't mean it's easy to bring up: According to The Discover® and Match Group study, most people would rather discuss their finances than their exes on a first date. And oftentimes, this aversion to talking about past relationships never really goes away, even after you've been dating for a while.

But being open about former flames is a great way to gain insight about your SO's non-negotiables.

Engaging in open conversations about these subjects early on prevents both of you from wasting precious time and ensures that you're on the same page right from the start.

Having tough conversations can be hard, but the facts suggest that it's important to address certain things sooner rather than later. This could include your credit score. Discover offers a Free Credit Scorecard, and it won't impact your credit score. It's totally free, even if you aren't a Discover customer. Check yours in seconds. Terms apply. Visit Discover to learn more.