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When you first start dating someone you’re really into, every convo feels exciting and special—hours pass in what feel like minutes, and minutes feel like seconds. But several months (or heck, several dinners) in, once you’ve gotten to know your partner on a truly intimate level, you might feel like you’ve run out of questions to ask them.
You’re not doomed…but you do want to proactively turn that boring conversation upside down. Because no matter how long you’ve been with your partner, keeping those deep, riveting talks alive and well is incredibly important for a happy relationship.
Take it from Terri Orbuch, PhD, author of 5 Simple Steps to Take Your Marriage From Good to Great and professor at Oakland University in Michigan, who has been following a set of over 370 couples for the past 30 years.
“Happy couples are intimately familiar with each other’s inner lives and social worlds.”
“One trait of the happy couples [I’ve studied] is that they are intimately familiar with each other’s inner lives and social worlds,” she says. Talking is, of course, the number one way to do that.
Carrie Underwood and hubby Mark Fisher started out long-distance—and mastered the art of talking. Here’s how they’ve kept their marriage strong:
But…where do you start? Not with rehashing your morning run, venting over your to-do list, or bringing up concerns about your kids, says Orbuch. Instead, go for “the type of questions you used to ask when you first met each other”—think: less office politics and weekend plans, and more hopes and dreams.
These types of inquiries not only spark meaningful chats (that can, btw, re-create that first date, falling-in-love feeling), but you’ll also discover different sides of your S.O. and deepen your connection, no matter how long you’ve been dating.
So next time you’re with your partner, swap out the old “How was your day?” with one of these expert-backed questions to ask your boyfriend (or girlfriend):
If you’ve been dating less than a year…
1. “Besides your parents, who shaped you the most during your childhood and teens?”
This question will give you insight into the most important people in your partner’s life, which might not always be obvious, says Women’s Health advisor “Dr. Chloe” Carmichael, PhD, a clinical psychologist in New York City and author of Dr. Chloe’s 10 Commandments of Dating.
2. “What’s the angriest you’ve ever been?”
Talking about emotions and what triggers them will always lead to an intimate conversation. Dr. Chloe recommends this Q to better understand what gets your boyfriend fired up.
3. “What are the telltale signs that you’re stressed, that no one else would know?”
Dr. Chloe recommends this question as a way to get insight into how your partner copes when things aren’t going well. Once you know, you can share your own signs and be better, more supportive partners for each other when the going gets tough.
4. “What are your guilty pleasures?”
This is a fun chance to find out how your partner likes to indulge, and what might be a little embarrassing to them. Whether it’s bad reality TV or sour gummy worms, you’ll usually get a look at what comforts your person or reminds them of their childhood.
5. “Who was your first love, and why did it end?”
Dr. Chloe suggests this question to help you understand your boyfriend’s relationship history. How he answers will show you what he values in a partnership and what behaviors are most hurtful to him. (That’s super valuable intel, btw.)
6. “When you were a child, what did you hope to be when you grew up?Why?”
This one is a classic for a reason. Talking about hopes and dreams—even if they’ve totally changed—makes you feel bonded to your S.O. (and them to you). And it shows you what they were interested in as a kid, a time you (likely) didn’t know them.
7. “When’s the last time you cried?”
This question can help your boyfriend open up about the things that make him emotional. Whether they were happy, sad, or angry tears, you’ll learn what makes them feel the feels, notes Dr. Chloe.
8. “What’s the biggest lie you’ve ever told?”
This line is bound to lead to an interesting conversation—one that may reveal what’s worth a fib to your partner and whether or not they regret being dishonest. Of course, they may not actually cop to their biggest lie, but whatever they do admit counts.
If You’ve Been Hot And Heavy For Over A Year:
1. “If you won the lottery, where would you travel and why?”
“This tells you all about your partner’s dreams for adventure and travel,” Orbuch says. Plus, it’s a fun opener that gives you a deeper look into their psyche without getting too intense from the get-go.
2. “If you could be anywhere in the world right this moment, where would you be and what would you be doing?”
“We want our partners to be authentically curious about who we are on our deepest levels,” says relationship expert and psychotherapist Gin Love Thompson, PhD. But asking your significant other to share his or her innermost thoughts and desires over appetizers can be a little, well, intense.
“Keep it light and fun while increasing the energy and excitement by starting a heavier chat with an icebreaker question like this,” Thompson says.
3. “Remember when we [insert sexy memory here]?”
Count on sex to always spice things up. “Tell your partner the intimate moments you’ve enjoyed most, and ask them to share their most memorable with you,” says Thompson. “Then, together, bounce around ideas of new tantalizing adventures you would both delight in.”
Not only will this liven up pillow talk, it’ll also help reinforce that you’re still hot for each other (and always will be).
4. “What makes you feel connected or disconnected to me during sex [or the day-to-day]?”
Sometimes a level of directness can help you go deeper—especially when it comes to the most intimate parts of your relationship. “I hear all day from couples that they harbor a sense of disconnection that they often don’t say out loud,” says Brandy Engler, PsyD, a relationship therapist in Los Angeles.
“These kinds of questions help people put words to what they want and how they want to feel—it taps into your core longings.” Getting this direct might feel awkward at first, Engler says, but ultimately, talking about things that divide you will bring you closer.
5. “If you were able to work in any other job for a year, what would it be?”
“This is a fun question that reveals what your partner thinks about, as well as their challenges and values,” Orbuch says. (Which are all evolving things, at least for most people.) “It also might reveal what your partner was thinking about when they were younger—dreaming about what they would be and do as they got older.”
Not only do questions like this open up the conversation to what your S.O. is secretly dreaming about, they also help you revisit a part of their past you might not have talked about in those early days.
6. “What’s stressing you out the most this week?”
With this question, “you’ll find out what keeps your partner up at night,” Orbuch says. Whether it’s a small annoyance with a coworker or a more serious issue, these worries define what stresses your boyfriend or girlfriend out.
“When you’re familiar with your their challenges, you’re better able to cope with their emotions.”
“When you are familiar with your partner’s present challenges, you know what is troubling them and you are better able to cope with their emotions,” Orbuch explains. “You’re better able to help them if needed, which creates a deeper bond.”
7. “What’s your biggest goal for the next 10 years?”
Aside from sharing your dreams and ambitions, this question also helps you start a conversation about compatibility—how similar are your goals, do the futures you envision look similar? “It helps figure out where they think they are in the arc of life,” Orbuch says.
While this is a great Q to ask early on in a relationship, it’s also one to go back to as things get more serious, since their aspirations could change.
8. “What is the one thing you want to be remembered for?”
Like those questions you probably asked in the early days of getting to know each other, this question helps you discuss your underlying values, Orbuch says. “You find out how your partner defines themselves—how they see themselves,” she says.
“This says, ‘I really want to know you better and I’m paying attention to who you are'”—something that your other half can forget when things become a little routine.
9. “How are you?”
It sounds overly simplistic, but “one of the deepest questions we can ask our partner—when done with sincerity and an intensive listening ear—is ‘How are you?’” says Thompson.
When you ask this, make eye contact and don’t interrupt—it’s as much about the listening as asking the question. “In the ultra fast-paced world we live in daily, we can lose sight of what our significant other is encountering on a personal level, be it at work, with the kids, or among family and friends,” Thompson explains.
The conversation can go to depths you’d never expect. “This is an act of love, and this support can enhance all areas of your relationship.” So ask it today, and ask it often.
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