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7 Things You Should Bring Up on Your Next Date

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First dates serve several purposes: they’re a chance to meet in person, flirt and see if there’s any chemistry. However, that first meeting is also the perfect opportunity to playfully grill your date.

With that said, you don’t want the date to come off as a job interview. Not sure what to say? Here are a few fun, open-ended talking points to bring up on your next date.

1. What are you really passionate about?

This is a thousand times better than asking, “So, um, what kind of stuff do you like to do?” Most likely, they’ve listed their basic hobbies in their profile write up. Also, people are usually way less nervous to talk about things they’re really passionate about, which is why this is a great ice-breaker question. It’s also a perfect opportunity to see what really excites the other person and see how they jive with your own interests. Perhaps you’ll get swept up hearing about your date’s backpacking trip through Vietnam or cringe inwardly when they mention that their life’s passion is taxidermy. Maybe you’ll feel super awkward when they just sit there and tell you quietly, “I’m not really passionate about anything.” Either way, this question is going to tell you what you need to know.

2. Who in your family are your closest to?

This is a great alternative to the usual, “Tell me about your family.” Families are complicated, so there’s always a chance that the person you’re on a date with won’t want to talk about his or her estranged relatives. By asking them about who they’re closest to, they get a chance to highlight the positive aspects of their family life, sparing them from rehashing old wounds and drama with someone they barely know.

3. What were you like in high school and/or college?

This is a great question to ask, provided you have a few years of buffer since you graduated. Ask them what they were like when they were younger and how they’ve changed. Were they the class clown? The popular quarterback? A nerdy loner who blossomed in college? It’s always interesting to find out how someone saw themselves in the past and how they see themselves now. It provides you with a glimpse into how they’ve experienced the world and their capacity for self-awareness.

4. What are you dying to try?

White water rafting? Hiking Mount Kilimanjaro? Spending a month in Paris? Trying the infamous “heart attack platter” at the local diner? It’s always great to get a peek into someone’s dreams and ambitions to see how they mesh with your own. For example, “I’m dying to go on a culinary tour of South East Asia” may sound a heck of a lot more appealing than “I’m dying to build my own composting toilet.”

5. What was your longest relationship?

Although a lot of dating guides advise you to not discuss your exes on the first date, I think it’s important to discuss some basic relationship history – especially if it’s a serious relationship you’re after. This is where you get to see if the commitment-aphobe red flag pops up. By asking someone about their longest relationship, you not only get a chance to discover whether they’re capable of having a long-term relationship, you’ll also get a sense of how they feel about their exes and commitment in general. For example, if someone says, “It was a month and she was totally crazy” – you might want to bounce.

6. When was your last relationship and how long did it last?

No one wants to be a rebound. If someone says they just broke up with their girlfriend or boyfriend last week, they’re probably not ready to date – period. Unless you like emotionally messy situations that waste your time, stay far, far away.

7. Where do you want to be in five years?

I know this sounds like a job interview question, but it’s an important one to ask. If you’re looking forward to a future that includes a relationship and other personal achievements, you want someone who shares your mindset. In other words, you want to find out whether this person actually wants a relationship and is capable of forming long-term goals. If they tell you, “In five years, I hope to have moved up in my career and be sharing a home (and maybe a dog!) with someone I’m in a serious, committed relationship with” – this person is definitely boyfriend or girlfriend material. However, if they say, “I hope to be doing exactly what I’m doing now” or “living on an island, alone” – run.



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