Real Questions with Clare

S2 Ep. 4 How Can We Re-think Online Dating?


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This week, Stephen is my very special guest, and we share our experience of online dating. A dating app match can turn into months of messaging, and you still might not know the person at all. We get honest about what actually helped us move from Hinge chat to a relationship that felt calm, intentional, and safe, especially after years of being single in Christian spaces and carrying the weight of other people’s opinions about timelines, age, and “settling down”. 

Stephen shares what online dating felt like over time, including the burnout of stop-start connections and the risk of building a phone-based bond that falls apart the moment you meet face to face. We talk about why we chose to meet quickly, what made our first date unusually easy, and the intentional questions that helped us learn who the other person really is. We also unpack a key lesson for Christian dating: transparency is not the same as full vulnerability, and oversharing too early can blur wisdom and boundaries. 

We don’t dodge the tricky bits either. Faith mattered, church attendance mattered, and we explain why we nearly didn’t have a second date, how we reconnected, and what “respect for values” looks like in practice without pressure or performance. We finish with simple, practical advice for Christian men and women: be intentional, be consistent, don’t waste someone’s time, and pay attention to whether you feel safe with the person in front of you. If this helps, subscribe, share it with a friend, and leave a review so more people can find the podcast.

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