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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