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The Sweetest Approach

[Blind Gossip] This blind item is so sweet that it’s giving us a toothache!

An actress who first became famous after her role in a classic teen flick is now going through a divorce.

She was at an Oscar party when she was approached by an actor with whom she had worked on a project several years ago.

He told her that he was sorry that she was going through a divorce. He told her that she was a wonderful person with a kind spirit and that he always liked her. He said that when she was ready to date again, he would be honored if she would consider going on a date with him.

She thought that was such a sweet and gentle approach that she might actually take him up on it!

The Actor was definitely NOT James Franco.

Similar: Poop Police

Actress:

Actor:

Clues:

[Optional] If you could set her up with any actor, who would it be?

Reader Interactions

Comments

  3. CanaryCry says

    Alicia Silverstone for actress. Not sure about the actor.

    No dream pairings for this item.

  4. Kingofboggle says

    Alicia Silverstone
    Brendan Fraser

    Positive Alicia is right. Brendan is a total guess

  5. blueskies486 says

    Actress is Alicia Silverstone.

    Clue: The toothache line is from Clueless.

    Actor: No idea

  6. xXvalentinaXx says

    Actress: Alicia Silverstone
    Actor: No idea
    Clues: Cher said to Tai that she gave Elton a toothache because she’s so sweet in Clueless and ”Clues” is a reference to Clueless itself. And also the candy in the picture being mentioned in the movie? (maybe I’m just reading to much into the clues but it’s my favorite movie :D)

  15. RadiantA says

    Definitely Alicia Silverstone but who could the guy be? I’d love it if it was Brendan Fraser: they were so cute together in Blast From The Past and he seems like a really, really nice guy (maybe even nicer than her overbearing crunchiness deserves.) Related item is about her and she fits the bill for classic teen flick and current divorce and having previously worked w Franco. I’m sure there are more clues I’m missing.

  16. malkatz says

    Alicia Silverstone. The tooth ache quote is from Clueless. She was at the Vanity Fair Oscars Afterparty.

  18. spunkymonkey says

    Alicia Silverstone. The clue being “so sweet and it’s giving me a toothache”. There was a line line this in Clueless. My guess is the actor is from king Cobra as James and Alicia starred together in this movie in 2016. Maybe James Kelley?

  20. lovertine says

    Rebecca Gayheart

    Adrien Grenier?

    Toothache – she started in teen flick Jawbreaker

  21. Tracy511 says

    Alicia Silverstone
    Not Sure on the actor
    Gave him a sweet tooth is a line from Clueless

  23. bananaway says

    Actress: Alicia Silverstone
    Actor: Jeremy Sisto?
    Clues: “so sweet that it’s giving us a toothache” is similar to a line in Clueless referring to what Jeremy’s character said about Tai.

  24. Amethyst says

    Alicia Silverstone

    No clue about the actor.

    “So sweet that it’s giving us a toothache” is very close to a quote that Cher says in the movie Clueless.

  25. lagrange says

    Actress: Alicia Silverstone

    Actor: ?

    Clues: Toothache (from Clueless) and classic teen flick

  27. jackrabbit says

    Alicia Silverstone
    Drake Bell?
    Clues: “sweetest approach” the both did voice work on “The Nutcracker Sweet”

  29. HDNYC09 says

    Definitely Alicia Silverstone with all these Clueless references. Not sure about the guy…maybe Ben Stiller? Also single now, looks like his type, worked together on Tropic Thunder?

  30. redstilettos says

    Aww! Don’t know who this is, but this actress needs to go out with this guy when she’s ready. I’d say J Garner or Anniston, but can’t think of a classic teen movie either was in.

  33. Baileygirl says

    I’ll say Alicia Siverstone but no idea on the actor.
    He sounds like a gentleman who may have carried a torch for her-who knows. I say she should give the guy a chance.

  34. MrsBreeder says

    Alicia Silverstone. I’m going with Brendan Fraser; they were in Blast from the Past together.

  35. FreddyCellophane says

    Actress: Alicia Silverstone

    Actor: Nicky Katt

    Clues: Alicia wants to break off a piece of that Nicky Katt bar!

  40. calumsmom says

    Alicia Silverstone? Clues: She starred in “Clueless” (classic teen flick, which, btw, is an awesome movie) and one of the lines in the movie was “Says you gave him a toothache”. Not sure who the actor is.

  42. cactuspillow says

    Alicia Silverstone
    Brenden Frasier? Benicio Del Toro? No idea.
    Kind spirit.
    Keanu Reeves

  44. filthycop says

    Alicia Silverstone and…

    clues –

    I noticed him scoping you out.
    He was looking at me?
    Says you gave him a toothache.
    How’d I do that?
    He thought you were sweet.

  45. bowerybabe236 says

    Actress: Alicia Silverstone
    Actor: Drake Bell
    Clues: Nutcracker SWEET is the movie they were in together

  46. tiger13 says

    alicia silverstone (classic teen flick), not sure on actor

    she worked on ‘nutcracker’ sweet with Drake Bell… he seems a bit young for her but maybe?

  50. vanillasky says

    Actress is Alicia Silverstone who is going through a divorce. Don’t know about the actor. Clues: line from Clueless where she said she gave him a toothache is an expression that means you’re sweet.

  56. mycatsarefamily says

    Actress: Alicia Silverstone
    Actor: Drake Bell?
    Clues : Sweet =Nutcracker Sweet
    Classic Teen Flick= Clueless
    Btw: Clueless co-star Brittany Murphy was once in a Twix commercial !

  57. prissy says

    Alicia Silverstone. Dunno who the sweet guy is but the movie clueless will always be my fave movie.

  58. sowing says

    Actress: Jennifer Garner
    Actor: Joel Edgerton

    Clues: Garner was in “13 going on 30”, and her character loved a candy called Razzles. Edgerton costarred with her on “The Odd Life of Timothy Green”.

  60. a dumb idiot says

    Actress: Alicia Silverstone
    Actor: I’m guessing maybe Wilmer Calderon? They were in a project recreating scenes together with James Franco and they were in all three together.

  65. PinkFlamingo says

    The “toothache” reference is a nod to the line in “Clueless” where Cher (Alicia’s character) told Tai (Brittany Murphy’s character) that Elton had told her that Tai’s photo “gave him a toothache” because he thought she was sweet.

  66. gc02ef says

    All I can come up with is Alicia Silverstone and Drake Bell
    “Clueless”
    The Nutcracker “Sweet”

  67. eyeindigo says

    Jennifer Garner and Joel Edgerton.

    Starred in the Odd Life of Timothy Green. Super sweet movie. Another clue, teeth being reminiscent of his role in Bright…his orc teeth shaved down…the linked article to “poop police” is another clue for Bright

    .take him up on the offer girl!!

  68. madalaine says

    Actress: Alicia Silverstone

    Actor: Jared Leto

    Clues: Sweet/ toothache from Clueless

    [Optional] If you could set her up with any actor, who would it be? Breckin Meyer

  70. Ramalama says

    Alicia Silverstone
    Christian Slater? They were both in King Cobra witb James Franco.

  76. louisianagurl says

    Actress: Alicia Siverstone
    Actor: Drake Bell – From The Nutcracker Sweet
    Clues: line from Clueless, Sweet from the title of the movie, m&m’s with nuts, wording about a gentle approach, which is how she mother’s her child.