After a round of speed dating the women were treated to a fun night out where they had the opportunity to get know a group of eligible bachelors.
But after watching the ladies in action, Matthew wasn't convinced Sheridan had fully let go of her past relationships, so decided to have extra one-on-one time with her to ask why vulnerability was such a problem for her.
"Stepping into the ring with dating, no problem, it's further down the track that the push starts," she said before tearing up.
"And I know I do it. And I know I have to stop doing it. But I don't think it's always been there."
When asked why the vulnerability problem started, Sheridan admitted that is began just six weeks into her second marriage, when her "self-esteem was destroyed".
The 41-year-old mother-of-two went onto explain that she discovered things were going on behind her back, and it made her feel like she wasn't good enough.
"I kept finding more and more things as time went on. I kept digging because I couldn't stop myself and I should've," she said through tears.
Matthew explained that Sheridan needs to give the Single Wives experiment everything she has.
"You giving your all is the beacon that shows the best men where you are."
The Single Wives continues Thursday night on 7
This week in TV podcast Binge List: The Handmaid's Tale, Sheldon and Amy's wedding in Big Bang Theory, Sacha Baron Cohen's Who Is America?, Wentworth axed, and UnReal season four. Subscribe on iTunes http://po.st/syE3JF, OMNY http://po.st/hxjAhm or listen below: