Dear Wendy
Dear Wendy

If They Asked: Should Oprah Give Money To Her Long-Lost Sister?

I’m introducing a new feature on DearWendy.com today called “If They Asked.” The idea is that we discuss the advice we’d helpfully offer celebs and people of note if they asked for it. Like, if Gwyneth Paltrow were to ask us how she could improve her reputation and re-endear herself to the American public, we might advise her to shut the fuck up about how hard it is for her to squeeze in five hours of exercise and manage to get her hair blown out every day. Or, if James Franco asked us if he should release a sex tape, we would tell him that yes, yes he should. After the jump, we address the big fat elephant in Oprah’s living room: should she give money to her long-lost sister?

On her show yesterday, Oprah revealed a huge family secret: she has a half-sister named Patricia whom she only learned about in November. Back in 1963, Oprah’s mother, Vernita Lee, gave Patricia up for adoption. Oprah was living with her father at the time and didn’t even know her mother was pregnant. In 2007, after years of searching for her birth mother, Patricia saw a TV interview with Vernita Lee and when information she gave coincided with what Patricia knew about her birth family, she realized she might be Oprah’s half-sister.

Can you imagine? You’re a lower-middle class woman working two jobs to support yourself and one day you’re just watchin’ TV when you realize the richest, most powerful woman in the world is probably your sister?! But to her enormous credit, Patricia never went to the media with her story. Instead, she spent years trying to reach out to her birth family — to her mother and to Oprah herself — with no luck. Finally, she was able to track down a niece and when DNA testing revealed that they were indeed related, she was finally reunited with Oprah and the rest of her birth family.

“She never once thought to sell the story,” Oprah said when she tearfully introduced Patricia to her audience on Monday’s show.

“Family business should be handled by family,” Patricia said. “It couldn’t be handled by anyone else. That’s not fair.”

So, the big question is: now that Oprah has been reunited with her half-sister, a woman who has already proven herself to be more trustworthy than most people Oprah has allowed into her inner circle, should she give her some money? Oprah’s worth billions, after all, and her sister is still working two jobs to support herself. She kept a secret that she could have sold to some media outlet for thousands — maybe hundreds of thousands of dollars. Oprah’s deceased half-sister, also named Patricia, once sold the story of Oprah’s teen pregnancy to a publication for $19,000, which devastated Oprah. But this Patricia didn’t sell her sister out like that. She kept the secret and she seems genuinely interested in forming a relationship with her birth family, which in addition to Oprah, includes their mother as well as nieces, nephews and cousins. But can a true relationship really be formed when Oprah is so filthy rich and her half-sister is financially struggling? Won’t such a drastic difference distance them?

If she asked, this is what I’d tell Oprah: give your sister a one-time chunk of money — a million bucks or something like that (pocket change to Opes). Give her enough to pay off her debts, pay off her kids’ debts, and donate a sizable amount to her church (Patricia is a very active member of her church and credits her pastor for helping her track down her birth family). Give her enough money that she’d be crazy to ask for more, so if she does, you’ll know she isn’t the genuine person she seemed to be. And if she never asks for money, you’ll know she’s provided for and that she was worthy of what you gave her initially. If nothing else, she should get something for being part of what was surely a huge ratings-boost during a pretty lackluster final season. Let’s face it, Oprah, your trip to Australia was kind of a snooze fest. A big family secret was exactly what you needed to finish your series with a bang and the one responsible should be rightfully rewarded.

What do you guys think? Should Oprah give Patricia money? If so, when and how much?

46 comments… add one
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    jdoublejj January 25, 2011, 9:42 am

    I didn’t even finish reading the entire column before I fell out of my chair. Absolutely the best advice you could give to Gwyneth Paltrow. And it was a perfect use of language. It’s like you plucked the words right out of my brain. I now feel validated. Good times. Now to read the rest of the column, lol.

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  • MellaJade January 25, 2011, 9:51 am

    Hey Wendy, Congrats on your new site! As to Oprah, I have to agree with your idea of the one time lump sum gift. This sister seems to be on the level – maybe Oprah will offer to send her new nieces & nephews to college or something too.

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    • Black ivy August 20, 2022, 5:06 pm

      I agree with you to an extent Wendy I definitely think she should give her money so that her children or taking care of she’s secured but more so I think that you know even in rebuilding a relationship with over having such a platform she could teach her sister how to become a boss of her own it goes to make something of her own you know what I’m saying so that she’s making her own way and I think that would be way more beneficial than just paying her bills and also because of that sounds learning from Oprah I mean her connections are limitless but you know what her sister has much to offer as well because life lessons are just important I also agree that she should definitely get some money because it was snoozefest and what blew it up I mean everybody was tuning in to see this what Oprah Winfrey has a long lost sister I got to see this it couldn’t have been better for her is unbelievable you know and she definitely banked rolled off of that so definitely agree with you on that point and she did not come in money snatching and it is completely natural for someone who is adopted to later on in life want to reconnect with their birth family it just so happens that hers is Oprah Winfrey you know it doesn’t change the fact that she wanted to find her roots and that’s natural
      -Black ivy

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  • Amber January 25, 2011, 9:52 am

    I agree with what you said. She did help boost Oprah’s ratings and the one time lump sum would be like an appearance fee. I know if I somehow came in to millions I would want to help my family get out of debt. From what I saw on Oprah I believe that she would be content with whatever Oprah gave her and just happy to have family to share her life with.

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      Wendy January 25, 2011, 10:05 am

      I agree; her sister seemed so genuinely sweet and just really excited to have found her long-lost family more than anything else. That her birth sister is OMG Oprah is almost beside the point. Almost.

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  • baby.blanka January 25, 2011, 10:23 am

    LOVE (love, love, love) the new column idea! I had to stop myself from laughing at my computer! Really looking forward to the upcoming articles as I have a feeling I will have a new favorite “mental health break” website.

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  • TheOtherMe January 25, 2011, 10:25 am

    I don’t think Oprah “owes” any set amount to her (half) sister. I believe she would WANT to help her in any way that she could, financially or otherwise. I think it would be a great gift to relieve her sister of the financial stress she is currently living with so she could be more available to spend time with her family. Often times greed gets in the way of family relationships but in this case, it really doesn’t seem to be Patricia’s motive.

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    • Kaiser Söze January 25, 2011, 12:34 pm

      Good points.
      Good to see you here, TOM!

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      • TheOtherMe January 25, 2011, 2:32 pm

        Hi & thanks ! good to see you too !

  • AnitaBath January 25, 2011, 11:09 am

    I completely agree, especially on the lump sum. I’ve been randomly thinking about this topic on my own.

    I mean, Oprah gives luxury cars to complete strangers in her audience. This is her long-lost sister, it only makes sense.

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    • camille905 January 26, 2011, 12:41 pm

      @Anita- That’s a very good point (the Oprah audience gifts). If I had money to give away to random strangers and a member of my family was struggling I would totally want to help them.

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  • Zoe January 25, 2011, 11:14 am

    I think Oprah will do it anyway, whether she feels like she has to or not. This is Oprah, who gives away millions and millions every year–her sister will be well-taken care of and will probably earn a job or five that will earn her more on top of that. This revelation will change absolutely everything for her.

    That’s so wonderful that she was so honest about the situation, too. Good people exist!

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  • Emily January 25, 2011, 11:37 am

    Yes, I agree too. I think she could give her a decent amount of “normal folk” money and it wouldn’t really even affect Oprah in any way but it would have a huge benefit to Patricia. And she seems like a nice decent person who is very hardworking, as you said. I hope they can build a relationship from this – I felt like Oprah was so boggled by the whole thing, she kind of treated Patricia like any other guest on her show. But it would probably be very hard to trust ANY new person, let alone someone you just found out is your half sister.

    In Oprah speak, they just need to build some bridges together and maybe they can build those with cash! 😉

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  • ladiejoy January 25, 2011, 11:39 am

    How weird is it that both her sisters were Patricia? Anyway, I agree – knowing Oprah’s ethics I’d be shocked if she didn’t help her out financially. I mean come on… if I found out Oprah was my sister, I’m not gonna lie… I would hope she’d help me out though I wouldn’t actually ASK for it.

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    • delilahgem January 25, 2011, 12:38 pm

      Yeah, I don’t think I could actually ASK for it either. But yeah, as much as Oprah does for strangers, you would think she’d take care of her new family.

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  • XanderTaylor January 25, 2011, 11:41 am

    Awesome column! You are going to do great on your own! I think Oprah should help her financially through an annuity that will give her a set amount of income for the rest of her life. It would be great to help out any nieces & nephews as well. The comment on Gwyneth was spot on.

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  • Rachelgab January 25, 2011, 11:50 am

    Knowing that Oprah supports her mother and father –who she doesn’t seem to speak too highly of, she probably will give her new sister some cash and prizes just cuz. I agree with what some others said, she definitely doesn’t owe anyone anything, but I wouldn’t be surprised if Patricia and her family start getting to go on some nice vacations and maybe get help with some debt or a nice Birkin bag as a birthday present.

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  • Kristen January 25, 2011, 11:58 am

    I think she should give her the lump sum just like you suggested. She would give herself a bad image if she didnt. I do think she should prove that this women is ACTUALLY her 1/2 sister first so there arent a ton of “Other 1/2 brothers and sisters” coming after her

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    • camille905 January 26, 2011, 12:42 pm

      Ummm….I thought she already proved that with a DNA test? Read the article a bit more closely.

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  • Allyson January 25, 2011, 12:01 pm

    I wouldn’t tell Oprah to give her money – that’s so impersonal. This is a long lost sister who has never asked for anything. I’d maybe pay off her debt, buy her a house, give her a job on my set, but to flat out give her money? Just seems cold, almost like she’s paying her off to stay out of her life.

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  • Laura Matthews January 25, 2011, 12:06 pm

    If it’s a lump sum, I think Oprah needs to set up some sort of fund that pays out monthly amounts, rather than one huge amount entirely available at once. Going from poverty to millions isn’t that great if you’re not already accustomed to that kind of money and attention. People will be after Patricia for money once they know who’s in her family, not to mention the tax implications. Patricia needs to be guided through the transition if it’s to be a blessing to her. Sounds like she has a strong character though, so will do fine with the wisdom and guidance of her big sister.

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  • Katy January 25, 2011, 12:11 pm

    Did anyone else get cringey during the homevideo they showed of the “first meet thanksgiving” where Patricia runs over to hug, and hug, and hug, and hug Oprah and Oprah kind of seems like “dear lord get this woman off me this is too too much!” ?

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      Wendy January 25, 2011, 1:15 pm

      Yes! But I tried not to read too much into it. I’m sure it was a spectacularly strange thing to greet a long-list sister you only learned about days earlier AND have it be video taped for millions of people to watch. I really think once Oprah processes all this — and remember, Patricia has had three years to process the information — she’s going to find a true and trustworthy confidante in her sister. And for a woman in her position, that’s got to be worth a lot.

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    • AnitaBath January 25, 2011, 3:19 pm

      I think, like Wendy said, she’s already mostly proven herself to be trustworthy. It seems like she tried to do all of this confidentially and didn’t sell the story or anything, it seems like it was up to Oprah to put the story out there. Oprah seems pretty excited about it, especially considering how crappy most of her family has been so far.

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  • TheFabulousmzm January 25, 2011, 12:19 pm

    I have half-siblings that I’ve never met. I wonder if any of them are Oprah!

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  • Nuttin January 25, 2011, 1:12 pm

    I have a sister that’s a millionaire. I wouldn’t take a dime of her money as I WOULD HAVE TO HEAR ABOUT IT FOR THE REST OF MY LIFE.

    Every B-day and X-mas I would hear “hey remember that cool mil I gave you. I bet I sure helped your life…blah blah blah. I think Oprah is the type who would do the same since she never stops talking about all the things she has given people.

    If she offers it great, but don’t take it.

    On a side note: Yes I have issues with my sister.

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    • TheGirl January 28, 2011, 10:40 am

      Great point!! Oprah is totally one of those people that would constantly point out what a great thing she did and how awesome she is. I guess you have to weigh whether the monetary help is worth it or not – I would say it is, just for her kids’ sake. Take money for their college education and that’s it.

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  • HelloJello January 25, 2011, 1:39 pm

    Obviously Oprah doesn’t HAVE to give anyone money, but like many other said, I would think that she would want to, at the very least ease some of the burden that her new-found sister has been experiencing. I would lean more towards paying for specific things, rather than giving her an lump sum of money. Pay off some debt, help put the nieces and nephews through school, that sort of thing, and maybe reassess later. Maybe I’m too jaded. But if Patricia is as genuine as she seems, that sort of thing would be greatly appreciated.

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  • Marie January 25, 2011, 2:37 pm

    Yes, I think she should give her some money, but as a one time gift, Oprah has earned all her money via hard work, it is not some family inheritance she is keeping from her. I think $100K one time gift is sufficient, maybe buy her house or pay off the mortgage so she has somewhere to live.

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  • AnitaBath January 25, 2011, 3:53 pm

    I just read this quote from Oprah on a People.com article:

    “I had her to dinner at my house the night before we taped the show,” Winfrey said, where there were “conversations about [Patricia’s] family and how I can be helpful.”


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  • ArtsyGirl January 25, 2011, 4:04 pm

    Hmm a rather large conundrum about families and money. I think if I were in Oprah’s shoes I would offer to help out the family (i.e. pay for her nieces and nephews to go to school) and maybe offer to pay off debt, but at the same time Oprah is a self-made billionaire. She came from extreme poverty and pulled herself up by her bootstraps. It is not like she inherited the money from a family member so there really is no level of entitlement for her half-sister. I imagine she will help out Patricia, partly out of goodwill but also partly due to the press. I mean she brought her half-sister into public and knew that it would come out that she is struggling.

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  • Schwinny January 25, 2011, 4:37 pm

    I would suggest getting to know her sister better, which she obviously will do, and giving her a job somewhere within the Empire that suits her sister’s talents and pays a salary that lets her not worry about money anymore. That’s so much more valuable than just a pile of money.

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  • Catie8 January 25, 2011, 4:45 pm

    First time poster here! I love the idea behind this sort of column. Like many of the other folks above, I imagine that Oprah will probably offer to help out with some big things: any major debt, Patricia’s children going to college (set up some sort of trust fund so they don’t have to go into debt to attend school), and help Patricia transition to working one job rather than two. I would hope that Oprah’s focus on the fact that Patricia didn’t sell the story helps is a very concrete suggestion of Oprah’s feelings of sisterly kindness, and likely any monetary gift will reflect that rather than obligation (such as some larger lump sum that feels like a pay off).

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  • Sarah Brown January 25, 2011, 4:46 pm

    I have been giving Gwyneth this same advice in my head for at least a decade.

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  • Lexington January 25, 2011, 7:09 pm

    I think it would be cool if she helped her out- I mean what is family for? But at the same time, if I was her sister, I would be really cautious about accepting any money at first because I would be trying to connect with my sister and I feel like that would just set a bad tone to the relationship. Now, a cushy job offer/recommendation, that I would take.

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  • BeccaAnne January 25, 2011, 8:34 pm

    oooo I like this new feature.
    I think presents not in cash form would be better (house/pay off debt/fancy job/send the kids to college).

    And how exciting to reunite with family!

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  • Leyahn January 26, 2011, 9:59 am

    The line that struck me most in this article was “Instead, she spent years trying to reach out to her birth family — to her mother and to Oprah herself — with no luck.” So Oprah and her handlers wrote Patricia off as being a crackpot for all those years and Oprah’s mother, what, didn’t want to admit that she gave a baby up for adoption? Not until the niece agreed to a DNA test was Patricia accepted as “family”.

    Wow, if I were Patricia I would want nothing from Oprah. If I were Oprah I would be ashamed that I didn’t give any interest to her claims from the get go – really, with the huge legal team Oprah has she could not spare one of them to investigate Patricia’s claim?

    That being said – Oprah’s reputation has been built on her largess to strangers- one would hope she would want her half-sister to have an easier life like she has provided for so many strangers over the years.

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    • camille905 January 26, 2011, 12:46 pm

      At the same time though Oprah’s mother lied to her about the existence of this half-sister so what was she supposed to do? Believe a random stranger over her (admittedly shady) mother? And she had been terribly hurt by another half sister in the past. There is nothing wrong with being cautious after all Oprah has been through.

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    • katie January 27, 2011, 6:16 am

      Yeah, um, can you imagine how many people have tried to contact Oprah with shady things like this? Famous people always have psychotic fans that try to approach them or contact them. Chances are that this wasn’t the first time someone had said something along these lines, and more than likely it never even reached Oprah’s ears as a serious inquiry. Paired with the betrayal of a half-sister in the past, there’s really no reason to think badly on Oprah. I would be skeptical of people claiming to be related to me, even if it were possible it were true; Oprah didn’t even know that this woman existed. As for her mother, that’s a different story, but not Oprah’s fault.

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  • Bill January 26, 2011, 10:15 am

    I think Oprah used her sister for ratings.

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    • Titsmagee January 29, 2011, 3:04 pm

      I wholeheartedly disagree…and wish you had given reasons for that conclusion.

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  • Kate January 26, 2011, 2:03 pm

    …if I remember correctly, many moons ago, when Oprah was just a millionaire, she gave her friend Gayle a million so they both could be. In those days she was more open with details of her life, and I don’t imagine she’d be as forthcoming today, nor do I think she needs to be. anyway, if the past is a predictor of the future, maybe it’ll happen. and good luck to Patricia: she and her kids seem like class acts.

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  • Wolvie_girl January 26, 2011, 4:10 pm

    I think the better way to give a family member a gift of support would be in the form of an irrevocable trust. This way, you can put limits on how and when the money is spent to ensure that the money is used wisely for debt and future generations, rather than blown on extravagant shopping sprees.

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    Katie January 29, 2011, 2:03 am

    Hey Wendy, i read your stuff all the time on the frisky, and i love the new website and i love this new column. im gonna have to really keep up on current events now (that gwyneth paltrow comment totally went over my head! lol) so i can read it whenever you post it. its a great idea.

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  • Titsmagee January 29, 2011, 3:03 pm

    If NOTHING ELSE, Patricia’s Christmases are going to be so fucking awesome from now on.
    “What can I get you for Christmas, new sis??”
    “Oh you know, any number of your favorite things.”
    “How ’bout all of them?”
    But then of course she has to get something for Oprah now…*groan*

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    • Delilahgem January 30, 2011, 4:22 pm

      Lol Tits!! I read your comment and the whole time I though, “how do you pick out a gift for Oprah?” I mean really, a coffee mug with a picture of the two of you?

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