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I know of two instances of Data attempting a relationship before he got his emotion chip, first having sex with Tasha Yar early on in the series ("I'm programmed in multiple techniques"), and secondly with crewmate Jenna in the episode In Theory where he fails at having a lasting romantic relationship.

But has he ever tried to have a romantic relationship AFTER installing his emotion chip?

Both canon and Extended Universe examples are acceptable.

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    He had that relatively brief flirtation with the Borg Queen in First Contact. – Paul D. Waite Jan 28 '17 at 9:06
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    Given that the only canon post-emotion chip are the three films, I think Paul has exhausted those answers. – ench Jan 30 '17 at 21:32
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    Yeah. Canon sources are slim pickings on this. That's why I opened it up to non-cannon/EU sources, particularly any novels that may have broached the subject post emotion chip. – iMerchant Feb 10 '17 at 5:52
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In the novels:

Yes

Specifically with a character named Rhea McAdams - who first appears in the book Immortal Coil. She makes another appearance in the 3rd book of the "Cold Equations" trilogy: "The Body Electric"

Set around the events of "Insurrection", McAdams comes to serve on the Enterprise-E and things happen and Data falls in love with her and they begin a relationship. Things happen and Data discovers that she is an android created by the immortal Flint for reasons and she decides to leave the Enterprise for reasons. Later (in 'The Body Electric') they meet again and Data is forced to choose between saving her life or Flint's (who is capable of resurrecting Laal) and it causes Data much grief over having to let her die.

https://memory-beta.fandom.com/wiki/Rhea_McAdams

IMO: Immortal Coil, Cold Equations trilogy, and the Immortal Coil follow-up (Light Fantastic) are excellent and well worth reading if you can cope with the fact that CBS / Paramount will never film these superior stories ;D

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