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He was engaged to Charles Augustus Milverton's housemaid. At the end of 'The Adventure of the Copper Beeches,' Watson writes "As to Miss Violet Hunter, my friend Holmes, rather to my disappointment, manifested no further interest in her when once she had ceased to be the centre of one of his problems."

Holmes does not show any sign that he had a girlfriend before he met Watson. Most of the time he has a suspicious air towards women based on the fact that he states more then once that you can't trust them.

Some of the film adaptations of Sherlock Holmes show that he does, like Young Sherlock Holmes (1985) and the latest Sherlock Holmes film staring Robert Downey Jr. (2009)

In the 2009 film, a character called Irene Adler is added to the story to be the romantic interest for Holmes. This character was taken from one of Conan Doyle's short stories called A Scandal in Bohemia. In that story Holmes ventures in a disguise to Irene's home in search of an important photograph. The story is interesting and Irene's character is memorable because of the fact that she ends up being the only woman ever to outwit Holmes. As it turns out Holmes is impressed by the lady and keeps a photograph of her in memory of the case.

Although a lot of people over the years exaggerate upon Irene Adler and Holmes, in the original story there is nothing to suspect a romantic relationship ever happening. In the story Irene marryies a man and leaves England.

This character was never fully brought up again in any of the Sherlock Holmes stories. Save only by name.

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Q: Did Sherlock Holmes ever have a girlfriend?
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