10 Thought-Provoking Questions To Know Close Friends More Intimately

Despite the breakup (which a source says came at the end of 2024), TMZ reports that Kaia Gerber & Austin Butler are on good terms, and that the relationship came to a natural end. The split also explains why Austin didn't join Kaia on her family New Year trip to Cabo San Lucas, despite the fact mom Cindy Crawford, dad Rande Gerber, brother Presley Gerber, and his girlfriend Isabella Jones were all there.

At the start of their relationship, a Peoplesource said that “she seems really happy" and "all of her friends think he's really cute." And as their relationship progressed, Kaia and Austin kept the details of their romance pretty private (similar to Austin's Dune costar Zendaya & recent fiancé Tom Holland), and told WSJ Magazine that “honestly, I feel like so few things in my life are private, and that is one of the things that I try to keep as sacred as possible."

The couple was very close for a long time, and spent “as much time together as they can,” a source told US Weekly. “Although Austin and Kaia are both in the public eye, they’re really down to earth and have a very secure relationship, so they never let jealousy or anything like that get in the way."

They also supported one another's work, with Austin showing up to Paris Fashion Week and Kaia attending The Bikeriders premiere. Hopefully they can still support one another as friends!

1. Questions To Ask If You're In The 'Honeymoon' Stage

Whenever we finally move from flirting with our crushes to being in a relationship with them, it's typically followed by a period of euphoria. You and your boyfriend likely can't get enough of each other right now which is probably making your friends playfully roll their eyes. Since everything is brand new, you can still keep it light though.

O'Neill suggests asking "open-ending questions that prompt curiosity and connection:"

• What's one dream you've never let me in on?
• What's one little gesture that can make you feel valued?

"These couple of queries facilitate bonding while generating enthusiasm for the goals and interests of each other," he says.

2. Questions To Ask After Your First Big Fight

Even if you and your boyfriend are super tuned in to each other, a disagreement or argument is bound to happen. In case you're worried, your relationship isn't on thin ice because you're not seeing eye-to-eye on something. O'Neill says you can ask:

• How do you think we handled the argument?
• What could we do differently next time to make our future fights more productive?

His reasoning is that these questions "promote growth and empathy" so "disagreements are transformed into stronger communication opportunities."

Note: Disagreements should never turn physical. It's not okay for you and your boyfriend to become physically aggressive with each other. If you're concerned about domestic violence, dial the National Domestic Hotline at 1(800) 799-7233.

3. Questions To Ask Before Introducing Your Boyfriend To Your Parents

Introducing your boyfriend to your parents is a huge step that can be scary and exciting. I was terrified when my parents first met my fiancé because they couldn't stand my ex. But, the conversation between them flowed and everyone always looks for him to be at family events.

If you're ready for introductions to be made, O'Neill wants you to "encourage the normality of preplanned talks" by asking:

• What is something about me that you think my parents would really love to hear about?

By doing this, he says it'll "help alleviate anxiety and ensure both spouses feel comfortable and attuned before meeting the parents."

4. Questions To Ask If You Or Your Boyfriend Have An Illness

It's never easy to experience illnesses or health scares, but it can be terrifying if you don't know how to help your partner manage if something unexpected happens. O'Neill says to "nurture insights with queries such as:"

• What is one thing I could to assist you better when ill?
• Are there any aspects concerning your healthy that haven't been discussed which make you anxious?

"The conversations provide a safe space for airing concerns while building up mutual support through health difficulties," he adds.

5. Questions To Ask If You're Worried About Boyfriend's Spending Habits

Financial red flags are always a cause for concern when dating someone — especially when it seems like your boyfriend doesn't care about his spending habits may affect your household if you live together. O'Neill suggests asking:

• What are your financial goals?
• How do you see us working towards them together?
• How do you feel about budgeting as a team?

This will "make goal alignment stronger" because "effective communication about finances can prevent misunderstandings," he says. Also, this helps "lay the foundation for a shared vision of the future."

6. Questions To Ask To Deepen Vulnerability With Each Other

Being vulnerable isn't easy for everyone, let alone two people in a relationship. It took me years to feel comfortable expressing my sadness or fears to my fiancé because I was afraid he'd think I was 'weak.' However, this can cause more harm than good because it becomes difficult for our partners to know what's going on with us if we don't open up.

O'Neill says you can ask:

• What's one fear or concern you've hesitated to share with anyone before?
• How can I help you feel safe sharing with me?

7. Questions To Help Move The Relationship Forward

If you're still wondering "what are we doing" after asking some of the above questions, you focus on asking the following "future-oriented questions," according to O'Neill:

• Where do you see us in 5 years?
• What's something you envision us doing together as a couple in the future?

Mac Duggal Halter Rosette Satin Maxi Dress

Ooh, so sultry! This satin maxi dress features a cheeky open back design that pairs perfectly with a flattering halter neckline. The big rosette decal on the front recalls Valentine's Day blooms in the cutest way.

RIXO Ardith Check Midi Slip Skirt

With bits of red and pink, this plaid midi skirt would be so sweet for a more casual V-Day date alongside an oversized sweater and some ballet flats.

Dolce Vita Linsey Heels

These deep red satin heels with pairs of rosettes on the straps are everything. They'd work well with a mini dress and blazer for a fun V-Day 'fit, though you could also easily wear 'em year-round with dress pants and a formal blouse.

Lace Rosette Tulle Tights

These floral tights will instantly upgrade any Valentine's Day get-up, especially if you plan on wearing a coordinating mini dress or skirt – they're meant to be seen!

By Anthropologie Colorblock Column Midi Dress

The bold color blocking on this midi dress is playful enough that you can wear the piece alone. It'll look great whether you dress it up with heels, or down with some comfy sneakers.

The Giselle Lace Bustier

If you feel like really dressing up this year, this lacy bustier top adds a very sexy-yet-elegant vibe. Pair it with some black slacks or a black skirt, then layer up with a sleek cardigan or jacket.

The Tilda Maxi Slip Skirt

When it doubt, red it out. The color is V-Day's perfect match, and this comfy maxi slip skirt makes donning it so easy. You can style it however you please – we'd rock it with a tucked-in graphic tee, a denim jacket, and some sneakers.

Coconuts by Matisse Florence Kitten Heels

Kitten heels will always be a winner in our book. This sleek pair features a tiny heel height, pointed toes, and eye-catching paneling with mixed materials. They'll instantly complete your Valentine's Day outfit!

Reformation Tancy Midi Dress

Reformation kills it when it comes to dresses. This one's dotted in tiny hearts to fit right in with Valentine's season. The sweetheart neckline is ultimately super flattering, plus the midi length of the piece gives you ample coverage so you can wear it to a variety of plans, from dates to Galentine's parties!

Endless Rose Sequin Mini Skirt

This fiery and feisty number is a statement piece all on its own. Wear it with a more toned-down black top and some tall black boots to complete the look!

The Kenna Mid-Rise Heritage Barrel Jeans by Pilcro: Valentine's Day Edition

These ever-trendy barrel jeans are adorned with subtle heart illustrations, so they're a perfect fit for the lovey-dovey holiday.

ALOHAS Tb.490 Rife Sneakers

Yes, yes, and yes! These pink sneaks detailed with some bits of red practically scream Valentine's Day. The mix of suede on the upper and the rubber soles is so cute.

The Hannah Seamless Textured Tank

This tank boasts a floral texture that makes it a great base layer for any V-Day 'fits you're planning. The red is the obvious choice for Feb. 14, though you can also shop this piece in 8 more colors!

Endless Rose Off-The-Shoulder Knit Mini Dress

We looove an off-the-shoulder moment. The knit material on this piece will keep you warm, but the silhouette still allows you to show a lil' skin.

Beach Riot Monterey Quarter-Zip Sweater

How cutesy is this sweater?! It's the perfect casual V-Day piece if your plans this year are simply to stay in and bake some delicious treats.

Maeve Bow Lace Turtleneck Top

This top was made for layering. Whether you wear just a bralette or a full-on tank under it, the sheer pattern boasts some adorable bows that feel extremely appropriate for the V-Day season!

Bibi Lou Bonnie Slingback Buckle Detail Heels

We can't get enough of these eye-catching heels. The bold buckle, block heel, and slingback strap instantly qualify them as a total "it girl" shoe for Valentine's Day.