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This Goes Out to our Extended Family Members…

June  30th,  2022
Caroline A.
By Caroline A. read
Posted in Culture

I am not the girl who gets asked “how are you still single?” Instead, I get asked, “why are you not doing more to put yourself out there?” Both questions just grind my gears, but there’s at least an implicit compliment in the first question that doesn’t even exist in the second. Is anyone else tired of essentially being told it’s your fault for not having a significant other, even though you’d like to? Even though you try, try, try to, as my mom likes to say, increase the flow of people through your life, hoping one might finally take interest? Welcome to my new campaign to end the use of these questions entirely. Instead, I’ll outline some alternatives here for how to catch up with someone about their dating life–without hurting them in the process.

  1. Starting the conversation.

Talk about literally anything else first! Do you actually care about this person’s life, their love to give, their highs and lows? Or do you just want to hear the gossip about who’s single and who’s not? I’d encourage you to check yourself before you wreck yourself, and make a point to have a conversation that shows your authentic care for the human being in front of you. Please make an effort to have a relationship with them, to pray for them, or to follow along with the rest of their daily life’s updates. Dating experiences, or lack thereof, can be a vulnerable thing for someone to discuss, and I can guarantee they’d be more likely to share if you already have a level of trust established.

  1. Maybe they’ll bring it up first!

If someone has a significant other that they’re excited about, it’s likely that at a certain point they’ll feel a desire to share that information without even needing to be asked. That makes your job so much easier! I highly encourage a certain amount of something common in the education field called: “wait time.” It might feel excruciating as you anticipate receiving new knowledge, but if you know you’ve got a problem with jumping the gun, try simply spending time with them and waiting for them to say something! 

  1. Alright, so they didn’t bring it up. Now what?

That’s it, you’ve gotta know! You’ve heard all the other updates, you see such beauty in them, and you desire for them to be loved because you love them so much. How do you finally ask about this person’s dating life?

  • Just ask.

“Do you happen to be dating anyone right now?”


Simple and sweet. There’s no need to include anything else that implies anything about why/what they’re doing wrong, or how every man in the world must be crazy for passing her over… It’s just not necessary. They can answer your question, and if they feel comfortable, it’s likely they’ll share more without prompting. They could say, “No, I’m not dating someone right now and I’m okay with that!” They could say, “No, I’m not dating someone right now, but if you know a good match, send them my way!” They could also say, “Yes, I am dating someone, and they’re amazing! Let me tell you all about them.” If they don’t feel comfortable expanding on the response, they can also just answer your question and leave it at that. And that is okay. Sometimes we have to stop ourselves and just try to be okay with someone else’s desire for privacy.

  • Make sure it’s appropriate in the context of your relationship with them.

Are you a female relative? A male relative? An old friend? A former boyfriend or girlfriend? A brand new acquaintance? An ex-best friend who’s still earning back trust? Please be conscious about the different levels of appropriateness which depend on who you are to them. Do you know if a family gathering or high school reunion is coming up? Be thoughtful beforehand, considering the most appropriate way to discuss this potentially sensitive subject. They will be so much more appreciative in the moment!

  • Show reverence for their response.

Praise God, you’ve been trusted, and you’ve now learned about your loved one’s experiences! This is something to be so grateful for, so why not express your gratitude to them? 

“Thank you for sharing that with me!”

“That sounds like a difficult experience, and I would love to pray for you moving forward.”
“I am so excited to hear how happy you are!! Let’s rejoice in how the Lord has blessed you, together!”

Now, all these ideas are simply that: just ideas. I am by no means an expert, and I’ve had to grow in these areas a lot myself. I cannot guarantee if you follow these steps exactly that you’ll magically receive the tea on someone’s dating experience. Every human person has the freedom to either respond or not, and in the end, you’ll have to respect that. However, I do believe that if you keep this blog in mind the next time you encounter someone to catch up with, that they’ll feel far more loved than the classic questions *sigh* we unfortunately hear every other time. Love is an exciting thing, and let yourself get excited for someone when it’s the proper moment. But out of your love for them, please try to love them well in these conversations, too. Good luck!

Caroline A.
Caroline A.

About the Author

Caroline is a 2020 graduate of the University of Texas with a B.S. in Chemistry. A true Texan and Catholic convert, Caroline wouldn't have dreamed of leaving her beloved state post-graduation. However, upon meeting the Culture Project at SLS20, she felt God was showing her what she never knew she needed. The radically different lifestyle of missionaries spreading a message of authentic love made it easy for Caroline to say yes to joining the family! "In each of our histories, we can identify exact moments when someone failed to love us. I'm excited to invite others to reflect on these moments and share with them the truth: they're worthy of a love flowing from their identity as God's beloved."


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