Jessie Woo Shares Details of Her Past Dating Life on Her YouTube Channel

Last Updated : November 30, 2023

Jessie Woo

The love for Jessie Woo was in the air at the start of this year as she also had dating experiences with two men.

She opened up about them to her fans through YouTube and shared her experiences.

Jessie Woo Had Dated a Man With Two Children

Woo became interested in a man whom she named David. He was much older than her, as the guy was forty-five years old. The surprising thing is that he had never been married. However, that man was romantically engaged in the past and is now the father of two grown-up children.

Even though she isn’t a big fan of going out with men who have kids, she decided to give it a shot because his kids were much older. She also felt that wasn’t a good sign as he had two children with two women in his 40s. Woo and that man also had a conversation about commitment.

Woo talking about her dating experiences with David. [Photo: Woo’s YouTube/Channel]

She had asked him whether or not he was afraid of commitment, and he thought he was scared, but as he was getting older, he wanted to have somebody by his side. The 45-year-old was a late bloomer, and success with maturity came to him later on in his life.

She came into his life at a good moment when he diligently sought to settle down. He was looking to purchase a home and showed her various houses when they were hanging out.

They built a really good, substantial conversation on their first date and had fun. Though he was involved romantically with two women, he doesn’t date that much. Woo had also asked about him from some of her friends who were also friends with that man.

They told her he was making great money and was involved in business. They bonded exceptionally for a week, but it didn’t work out because she felt the same patterns were repeating.

And they eventually stopped going out. All in all, she had a great experience with David, but they couldn’t stay in a relationship.

Woo Dated Another Man Who Asked His Previous Girlfriend to Be on IVF

After that, she dated another man whom she had named Timothy. She was also aware of his romantic life as she had researched about him. Further, that 50-year-old man wanted a baby boy and had put his previous girlfriend on IVF on her agreement.

Woo had dated a 50-year-old man who kept constantly sending her DMs. [Photo: Woo’s Youtube/Channel]

For her, that was a deal breaker and a red flag. She said that it was a sad and emotionally draining process to go through the IVF process even though they agreed to do it.

On their date, Timothy said he was fond of her personality and cared for her well. All in all, he was proud of her success.

Afterward, he pulled out his phone and took pictures of them, which she found annoying. Further, that man was Carribean, and Woo always wanted to have Carribean kids. She felt she could build a good home for their kids, as she was ready to be a mother.

She just went with the flow and enjoyed the date, but Timothy never hit her up after that date. One incident had happened at the end of their date.

When he dropped her home, a girl who looked like an IG model saw Timothy and excitedly approached him, screaming his name.

After that, they met once and just greeted one another, and she never went on a date with him again. But since then, he has constantly been in her DMs and comments.

Overall, Timothy was a no-go for her, but she tried hanging out with him, though he was a supposed red flag.

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She Needs Somebody to Build Generational Wealth For Her Future Kids

Woo doesn’t have a high preference for dating. She has also dated Caucasians and said she would love to date an Asian. Further, the girl has needed someone to support her as she has always been hardworking and busy. The YouTuber said she needed a man with a check, a CD account, and a little IRA for future benefits.

She has envisioned herself becoming a mom and stated that she has loved kids. Furthermore, she had been told several times that she’d have three children.

The lovely lady wants to be a mom more than anything else. And she needs somebody to help her build generational wealth for her future kids.

Moreover, the YouTuber said she needed somebody who loved Jesus Christ and would hold her in tough times. Furthermore, she is open to going out with people of different cultures. However, she doesn’t like going out with Asian men because of their upbringing.

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Spoke About a Bad Aspect of Interracial Dating

The YouTuber is also open to interracial romance, and she doesn’t have problems with Black men going out with girls of other races. She said that she has an issue with those black dudes who talk [expletive] about black women with women who aren’t black.

Woo shares her viewpoints about interracial dating. [Photo: Instagram]

What pisses her off is when they [expletive] the girl of another race and talk [expletive] about black women who is always at the front lines supporting them. And when they get gunned down, they are the ones who are going to be on the streets to protest.

Furthermore, she added that the women of her race are going to be the ones who will be bailing them out of jail. People in the comment section supported her, said it was facts, and presented their viewpoints.

Overall, she presented her viewpoint about interracial relationships but didn’t say that she doesn’t like them.