One of the trickiest things about dating is trying to figure out the right time to have certain conversations. For example, there are the burning questions, such as, "What are we?" and "Will you marry me?" for which the timing must be just right. But there are plenty of super juicy and illuminating conversations that you can never have too soon in a relationship.
Sure, most of the burning questions we have about our guy are not going to be great openers. But too often we avoid deeper conversations for fear that it would be too soon to “go there.” Love and marriage aside, you might be surprised to learn that most meaty conversations are totally OK to have whenever discussion drifts in that direction, even on the first date.
01. Tell me about your faith and values.
Most people go to great lengths to extract information about their date’s faith and values without ever having to actually have the conversation. This is totally unnecessary. You might notice that, even on first dates, you and your guy will let slip little clues about your politics, faith, or other moral codes. This is totally normal. Our values and, often, our spirituality dictate how we live our lives and who we are at our core. So next time your date mentions something about church or even politics, go ahead and go there. Ask him what church he goes to or how he feels about President Trump. His answers and the conversation that develops will hopefully be just the start of a deeper, more meaningful relationship.
02. What is your money personality?
Who says you should never talk about money on a first date? Our relationship with money goes way beyond how much we have (OK, maybe don’t talk about that). How we spend money and how we save it can tell us about the things we value, which is helpful to know about a person. So next time your date makes a remark about the overpriced drinks or tells you about how he splurged on an awesome vacation, use that as a jumping off point to discuss money personalities and what you each like to spend money on.
03. How do you unwind?
“What are your hobbies?” is a fine question, but what does he do when he isn’t volunteering or training for a triathlon? Aren’t you also curious about those far less glamorous moments of his day to day? Go ahead and ask your guy what he does to chill out. It’s totally fine, and even a little more enlightening, to ask your guy how he unwinds at the end of the day. Does he prefer to watch TV? Work out? Catch up with friends on the phone? These habits can be telling and can lead into many more fun topics, such as his favorite TV shows.
04. What are your parents like?
It’s hard to get to know someone well without getting to know their parents, too. It’s also pretty hard to get through a conversation about where you’re from without mentioning a little bit about your parents. So, when they do come up, don’t hesitate to ask for a little more information. “Oh, you grew up in Virginia? Is that where your parents are from?” “How did they meet?” Questions like this can help ease into more detailed questions about who your guy’s parents are. As with all personal questions, pay attention to the cues. If he doesn’t want to talk about his parents, he will divert the conversation, so don’t press too hard, and be ready to move along.
05. What was your family dynamic like growing up?
Maybe don’t use the phrase “family dynamics,” lest you sound too much like his therapist. But “Do you have any siblings?” is a basic enough question, and you don’t have to leave it at that. Dig a little deeper with questions like “Are you close with your siblings?” or “Were you close while growing up?” These kinds of questions can get you closer to a discussion about his family dynamics growing up, which is a great topic of conversation to discuss whenever it feels natural. How did his family spend quality time together? Where did they take vacations? Were he and his brother very competitive? Family and growing up can be a source of tension for some people who don’t have a lot of fond memories, so again, pay attention to the cues. But a lot of people really enjoy talking about their family, so it’s totally fine to give it a try.
06. Why are you still single?
This conversation may seem like a dating 101 no-no, but if you have a natural segue, why not throw it out there? These days, it’s likely you met thanks to a dating app, an online site, or a setup through a friend. What brought him there: Tired of the bar scene? Too busy with work to get out and meet people? Too many dead-end relationships? If the chemistry is right and you are feeling flirty, ask him how an attractive man like him is still single or how he found himself on Bumble (or whatever dating app you met on), and see how he responds. And no, you are not trying to find out what is wrong with him; you just want to know where he is coming from (yeah, go ahead and tell him that!). If he isn’t ready for it, he’ll say something evasive, and that is fine. You can come back to it again later.
Photo Credit: Cécile Bellu Photography