Blair Underwood is engaged to Josie Hart, his ‘best friend’ of 41 years

In June 2021, Blair Underwood and his wife of 27 years, Desiree Underwood, announced their split. Desiree filed for divorce and they made a joint statement, talking about their journey and their love for one another. They have three kids together, all of whom are adults now. Crash-cut to this month, roughly seventeen months after Blair and Desiree filing for divorce… and Blair is engaged. He’s engaged to a woman he describes as “friend” for 41 years.

Blair Underwood and actress Josie Hart are engaged after 41 years of friendship. The “Sex and the City” alum announced the exciting news on Instagram after walking the red carpet together for the first time as a couple.

“The most amazing, brilliant, beautiful, hilarious, thought provoking & insightful person I know who continuously lives life out-loud,” the actor captioned a picture of the two. “The future is crazy-bright Girl! None of us ever know where God will guide our paths. She’s had my back since before I even became an actor. When a 41 year friendship slaps you in the back of the head & blossoms into romance, you stand up, pay attention & step forward in gratitude.”

[From Page Six]

So now there’s a conversation happening about male-female friendships and whether Blair was cheating on his wife with his “friend” Josie and whether Josie is the mistress/jumpoff/special friend. We don’t know! I don’t know. I don’t live inside the When Harry Met Sally Cinematic Universe – I believe men and women can be good friends without anything romantic or sexual happening. But I also believe that there’s a good chance Blair was telling Desiree, “we’re just friends, nothing is happening” only to start up with Josie the second he was divorced.

Photos courtesy of Avalon Red, Cover Images.

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39 Responses to “Blair Underwood is engaged to Josie Hart, his ‘best friend’ of 41 years”

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  1. girl_ninja says:

    Welp. That’s convenient.

  2. Carnivalbaby says:

    I’m too old to buy this bullshit. He may not have cheated, and that’s a BIG may, but something was always there.

  3. Fernanda says:

    I mean… maybe they were really friends but never thought of something more but once the opportunity was there they went for it. I know from few of my friends once they were single again they got together with people they knew from before but saw them now differently. I wouldn’t judge Blair so hard. Unless some dirt comes out lol

    • Kate says:

      Also I imagine all famous actors have friends who are gorgeous – considering that’s usually a job requirement. You can’t fault someone after they are divorced for feeling attraction towards an objectively beautiful person?

      Also shouldn’t we be giving him credit for marrying an age-appropriate black woman?

  4. Erin says:

    I feel for the first wife. The moment you find out they’re engaged, you probably feel like you’ve been gaslight for 25+years!

    • ELX says:

      Unless it was the first Mrs. Underwood who didn’t want to look after him for the rest of her life. Sometimes it’s a case of a wife not wanting to stay married and an ex-husband who really liked being married—that kind of man will find another compatible wife quickly.

  5. D says:

    Men and women can absolutely be platonic friends. I’ve always been able to do that and have male friends for over 30 years. We are all married and know each others spouses and it’s just like having same gender friends.

    As for this situation, they may have just known each other and then when he separated from his wife they reconnected in a different way. Who knows. It isn’t like this is a week after he announced his divorce, it’s a year and a half! Let people live!

    • mel says:

      I am with you. I have some very close male friends, I also know their partners, and on top of it all, I’m single. It’s all fine cause you know…we’re grown ass adults with morals and values and those guys are like my brothers and vice versa. It’s VERY healthy to have friends of other gender.

      Also, in their scenario, you aren’t just starting to get to know each other…they had a head start of friendship and already knowing each other well. These things happen. Not everything is cheating.

  6. Elizabeth says:

    This reminds me of the Vince Gill/Amy Grant situation where they claimed to ‘be friends for years until one day, his wife found notes in one of his coats that implied there was some emotional cheating. On the other hand, a man and a woman can be platonic friends, but there must be clear boundaries once the friends marry or are in long-term relationships with other people.

    • cf86713 says:

      She shouldn’t have been surprised over this only because they had more chemistry in the House of Love video than the leads in the movie the song was for.

  7. Ari says:

    Ya’ll seriously? I was friends with my partner for 7 years and we were both engaged/in other relationships, never hung out alone etc. and when our engagements fell apart we got together fast. Until that moment I never looked at them like that. That is NOT cheating lmfao!

  8. Emmi says:

    I can only speak for myself (and everyone I’ve ever had that conversation with) but I have never gone in the romantic direction after feeling nothing. There’s a spark or a crush or something that can go away and develop into a 100% platonic friendship. I also have friends who were just that from day 1. I don’t know how you go decades without any romantic attraction and boom, there it is. I do know some people who were lying to themselves and admitted as much once they were in a relationship with their “we are just friends I SWEAR” person.

    • jbones says:

      It happened to me once.

      He was always a friend, and I was seriously involved with a guy, long term, who I was head over heels in love with. I NEVER saw my friend like that (a girlfriend once hinted at a hypothetical match and I cringed hard at the idea) NEVER thought he’d be my type physically, or otherwise. I get dumped and friend swoops in- BOOM. OH.My.GOD. Amazing.

  9. AppleCart says:

    Josie played one helluva long game.

  10. HeyKay says:

    I’m giving the stink eye to this news.
    Married for 27 years and suddenly the “friend” of 41 years is the brightest, etc, etc. and he is engaged?
    I feel for the Ex, 27 years of being gaslight is awful.
    Best of Luck to the Ex.

    • detnow359 says:

      “Friend” my aunt Petunia! There was more going on for those 41 years. It might not have been a full-on affair but something was there. That pic of the new chick says it all, like I finally got him, he’s mine! Frankly I wouldn’t want some female being close friends with my husband. That’s inviting trouble. People can talk platonic friendships all they want but at some point, somebody catches feelings, even if they don’t admit it. Poor Desiree. She always seemed like a nice woman. Never heard anything bad about her but I’m side-eyeing Blair on this one and I’ve been a fan of his since day one!

  11. Nicole says:

    Just as an aside. Blair Underwood used to live in my neighbor hood. Dayum that man is foine.

  12. Mrs Manganiello says:

    He’s so pretty.

    I believe too that men and women can be platonic friends and that’s it. I’ve had several men friends over the years and no romance or FWB situation happened.

  13. Mel says:

    Meh,, until someone has proof, I’m gonna say maybe it took 41yrs to see her that way. You’re married for years, you divorce, you spend a lot of time whining or whatever with someone and then stuff changes. I hate that everything is a “jump to conclusion”, for all we know, his wife ditched him because maybe SHE was over it. It’s a proven statistic that most divorces at this age are driven by the wife because she wants out.

  14. MissMarirose says:

    He’s 58. He got married when he was 30. It’s not that hard to believe that you want something different in a relationship when you’re young than when you’re middle aged and have already raised a family. I knew someone who married his friend after he divorced his wife of 30 years. He said it was more about companionship and comfort. That may be the case here.

    In fact, I have more respect for that than someone who turns around and marries some girl young enough to be his daughter.

  15. MsIam says:

    Well the ex-wife is the one who filed for divorce and there was no word of cheating, etc then. It sounds like their relationship ran its course. So they are both free to date, marry etc who they want. I think it is interesting that the fiance is referred to as Blair’s “best friend” but not the wife’s friend. I would not want to get in the middle of things by marrying the ex-husband of one of my friends. Maybe Blair and Josie had a friendship where they could talk about things but not hang around each other, they only saw each other occasionally, etc. It is a little “strange” but it does sound like a real life “When Harry met Sally”.

    • Myeh says:

      Relationship ran its course always sounds like one party used up all the advantage they could and when it no longer suited their fancy they dismissed the other who they always viewed as less and now view as remarkably unspecial

  16. Sue E Generis says:

    Hmmm, is this a Camilla-type friend? Because it sounds like that type of situation.

  17. Almonddanish says:

    Josie is 48 years old. I don’t know if he cheated but good on him for not dating someone in their 20’s.

    • molly says:

      I’ll give him credit for this too. Hopefully everyone is at peace and happy with the way things worked out.

    • MsIam says:

      How can that be right though? He said they’ve been best friends for 41 years meaning since he was 17 and she was 7. What 17 year old is best friends with a second grader?

      • Chanteloup says:

        oooo that would be icky. But why are we saying she is 48? When I google her, I get that she is 66 years old, 8 years old than he is. That makes a lot more sense if it’s accurate

  18. Joanna says:

    In my experience, someone always has feelings for the other in a platonic relationship. It’s never worked for me. And I have never been with a man who would be ok with an opposite sex friend. And I wouldn’t be either

    • Ange says:

      That’s a very narrow way to live and frankly it doesn’t speak well for any gender OR marital trust. I’ve had some very rewarding friendships with men and same for my husband with women. Even if there were feelings (there weren’t) we trusted each other to handle it appropriately but funnily enough it never came up.

    • Kim says:

      100% agree with Joanna.

  19. Joanna says:

    Blair Underwood in Sex and the City was so hot! Good looking man!

  20. Jennifer says:

    I don’t think we know enough to be able to judge on this topic if this was totally platonic or “flirty friends” or whatever. That said, I’d be surprised to go 41 years without a lick of sexual attraction and then suddenly, it happens. But sometimes you hear stories like that.

    Also possibly I’m biased because I wish the guy friend I have feelings for would change his mind. Yeah, yeah, I know, not ever going to happen (even though frankly, he acted like he had more than just “you’re like every other girl” going on with me for quite some time) and I’m trying to get over it and shut him out. Also, guys suck.

  21. Emily_C says:

    Wow, the assumptions here are ludicrous.

    First, you don’t totally stop being attracted to other people when you’re married. That’s not how it works. You stop acting on that attraction (unless you have an open marriage), but the basic attraction mechanism is still there. Being attracted to someone else is not cheating, and you can be attracted to someone you are truly only friends with.

    Second, he was divorced for a year and a half before getting together with someone else.

    Third, we do not know what his ex-wife thinks about this. It’s entirely in the cards that she’s a mature adult and is happy for them. Even if she isn’t, though, she doesn’t own him.

    Fourth, not allowing someone to have relationships with people of another sex/gender is abusive, and I have never known anyone irl who does this. Why are you with someone you don’t trust?

    • Formal Gumby says:

      @Emily _C: I don’t think he was divorced for a year and a half before getting together with someone else; I think it’s BEEN a year and a half by now, and he’s now engaged. Meaning, he got with someone else much sooner. Hopefully not during his marriage.

  22. Kim says:

    In my opinion and experience, there’s usually one side of the “platonic” friend set that would risk it all if they got the green light from the other one.