|Flirted with one of your party members to begin a romance.|
This achievement isn't possible to obtain until after you do your companions first major companion quest in Act II. Whenever you are given the "Heart" dialog option, make sure to select it. Do the party members companion quest, travel to your estate at night with them in your party, and then flirt with them and you should get this easily. See "Romantic" for more information.
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