What Happens When Dating and Work Collide? With Lian Zucker episode artwork

EPISODE · Sep 17, 2025 · 34 MIN

What Happens When Dating and Work Collide? With Lian Zucker

from Workplace Weirdness™ · host Maya Kadar Kovalsky

Welcome to Season 2 of Workplace Weirdness! In this episode, we share funny stories about workplace crushes, dating disasters, and cringe-worthy encounters that will make you cringe (and laugh) out loud.  Have you ever had a crush on a colleague or found yourself in an unexpected workplace romance? You might relate to this episode! We share experiences on workplace crushes, dating a coworker, and the awkward moments that happen when romantic relationships mix with professional life. We’ll talk about the dos and don’ts of dating at work, how to keep things professional while managing a relationship with a coworker, and how HR should step in when things get complicated. We also discuss workplace dating policies, the hidden dangers of dating at work, and what happens when that office crush turns into a full-blown romance. We’re joined by Lian Zucker, co-founder and CEO of Loop, who shares her take on navigating romantic relationships at work, setting boundaries, how to keep things professional when workplace dynamics start to get complicated, and how sometimes, things just don’t go as planned. So if you're looking for guidance on how to date at work without crossing any lines, or just want to hear some crazy stories about dating coworkers, you’ll love this one. Don’t forget to subscribe for more stories about office culture, workplace etiquette, and the weirdest HR moments. In This Episode: [00:00] Introducing Lian Zucker and Loop [02:51] The story behind Loop's inspiration [05:04] How Loop works [07:27] Building a company with family [09:03] Navigating workplace culture [10:35] Weirdest workplace moments [12:57] The week in work: Coldplay gate [19:26] Listener question #1: Setting boundaries with colleagues [24:26] Listener question #2: Struggles of a new manager [29:05] Cringeworthy question: Awkward office flirtations [32:41] Conclusion and guest farewell Notable Quotes [06:19] “Dating is less of a volume problem than you think, and much more so a problem of trust. When you get a warm introduction from someone you know or from someone in your community, you're much more likely to feel that trust.” — Lian Zucker [07:34] “My joke is often that the best thing I've done for the company is to convince my brother to build it with me.” — Lian Zucker [11:58] “Humans are so much more than checklists, and friends and matchmakers can really help you kind of overcome.” — Lian Zucker [14:12] “Infidelity is inexcusable. I think it's been equally disheartening to kind of see the schadenfreude involved a lot of public shaming, and ultimately their families were wrecked.” — Lian Zucker [16:35] “Historically, meeting in the workplace was very, very common. It can be a really great place to meet someone.” — Lian Zucker Lian Zucker LinkedIn -https://www.linkedin.com/in/lianzucker/ Loop - https://www.loopmein.me/ Maya Kadar Kovalsky Website - https://www.mayakadar.com/ LinkedIn - https://www.linkedin.com/in/mayakadar/ Workplace Weirdness Email: [email protected] SpeakPipe - http://speakpipe.com/workplaceweirdness Website - http://workplace-weirdness.com Instagram - https://www.instagram.com/workplaceweirdpod/ Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.

Welcome to Season 2 of Workplace Weirdness! In this episode, we share funny stories about workplace crushes, dating disasters, and cringe-worthy encounters that will make you cringe (and laugh) out loud.  Have you ever had a crush on a colleague or found yourself in an unexpected workplace romance? You might relate to this episode! We share experiences on workplace crushes, dating a coworker, and the awkward moments that happen when romantic relationships mix with professional life. We’ll talk about the dos and don’ts of dating at work, how to keep things professional while managing a relationship with a coworker, and how HR should step in when things get complicated. We also discuss workplace dating policies, the hidden dangers of dating at work, and what happens when that office crush turns into a full-blown romance. We’re joined by Lian Zucker, co-founder and CEO of Loop, who shares her take on navigating romantic relationships at work, setting boundaries, how to keep things professional when workplace dynamics start to get complicated, and how sometimes, things just don’t go as planned. So if you're looking for guidance on how to date at work without crossing any lines, or just want to hear some crazy stories about dating coworkers, you’ll love this one. Don’t forget to subscribe for more stories about office culture, workplace etiquette, and the weirdest HR moments. In This Episode: [00:00] Introducing Lian Zucker and Loop [02:51] The story behind Loop's inspiration [05:04] How Loop works [07:27] Building a company with family [09:03] Navigating workplace culture [10:35] Weirdest workplace moments [12:57] The week in work: Coldplay gate [19:26] Listener question #1: Setting boundaries with colleagues [24:26] Listener question #2: Struggles of a new manager [29:05] Cringeworthy question: Awkward office flirtations [32:41] Conclusion and guest farewell Notable Quotes [06:19] “Dating is less of a volume problem than you think, and much more so a problem of trust. When you get a warm introduction from someone you know or from someone in your community, you're much more likely to feel that trust.” — Lian Zucker [07:34] “My joke is often that the best thing I've done for the company is to convince my brother to build it with me.” — Lian Zucker [11:58] “Humans are so much more than checklists, and friends and matchmakers can really help you kind of overcome.” — Lian Zucker [14:12] “Infidelity is inexcusable. I think it's been equally disheartening to kind of see the schadenfreude involved a lot of public shaming, and ultimately their families were wrecked.” — Lian Zucker [16:35] “Historically, meeting in the workplace was very, very common. It can be a really great place to meet someone.” — Lian Zucker Lian Zucker LinkedIn -https://www.linkedin.com/in/lianzucker/ Loop - https://www.loopmein.me/ Maya Kadar Kovalsky Website - https://www.mayakadar.com/ LinkedIn - https://www.linkedin.com/in/mayakadar/ Workplace Weirdness Email: [email protected] SpeakPipe - http://speakpipe.com/workplaceweirdness Website - http://workplace-weirdness.com Instagram - https://www.instagram.com/workplaceweirdpod/ Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.

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This episode is 34 minutes long.

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This episode was published on September 17, 2025.

What is this episode about?

Welcome to Season 2 of Workplace Weirdness! In this episode, we share funny stories about workplace crushes, dating disasters, and cringe-worthy encounters that will make you cringe (and laugh) out loud.  Have you ever had a crush on a colleague...

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