The 35-year-old is pals with her ex-husband Ashley Cole and touched on their marriage in his new autobiography.
Before entering the house Jermaine told New! Magazine: "It's sad she's got a child and is now a single parent.
"I'm sure Liam will be there and give them both full support but it's sad for anyone in that position.
"So yeah, I feel sorry for her. I just hope she gets what she's looking for."
Jermaine has had plenty to say on Cheryl's love life, claiming the singer was 'still madly in love' with Ashley in his book Mental: Bad Behaviour, Ugly Truths and the Beautiful Game.
The former Girls Aloud singer divorced the footballer in 2010 amid reports he had been unfaithful after four years of marriage.
But ahead of entering the Channel 5 house, Jermaine spoke to Fubar Radio about the couple.
He said: "I think she’s still caught up over Ash."
Jermaine also addressed Ashley's infidelity during the marriage, adding: "I think that took a toll on her as a person as well."
After her divorce from Ashley, 37, Cheryl went on to marry Jean-Bernard Fernandez-Versini in 2014 after a whirlwind romance before divorcing two years later.
The singer then moved on to a relationship with former One Direction singer Liam Payne, 24, with the couple welcoming son Bear in March last year.
However, The Sun exclusively revealed the pair had split earlier this year.
Meanwhile Jermaine addressed reports he was to blame for leaking the story of Ashley cheating on Cheryl at the time.
He said: "Obviously Ash told me about it, and a certain someone else, and that friend was very close with Cheryl at the time, closer than I was.
"It was like well, 'It’s not going to be him', and the last person they looked at was me."
The outspoken star also claimed Cheryl used her divorce to boost her fame and Girls Aloud.
He added: "I phoned my friend explaining, saying, 'Look, don’t be surprised if it’s Cheryl'.
"Girls Aloud at that time was just coming out, so I thought that would be a good story for them, for Cheryl, for Girls Aloud, to promote themselves."
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