Holly O' Connor is the co-host of Miguel & Holly on Hot 101.5 FM in the mornings. She came on "Great Day Live" to discuss the latest trending topics with Kendall. Kendall and Holly shared in their mom guilt moments following Serena Williams tweet about missing her daughter's first steps. They also discussed Chrissy Teigen calling out a photographer for snapping her photo while she was pumping breastmilk in a car. Kendall and Holly revealed the weirdest places they pumped while they were nursing/working moms.