Originally Posted by Archaeolibris
Should I go out with her a few times just the two of us? Perhaps become intimate with her alone before bringing it up? That seems a little disingenuous if it's a decent part of my motivation. Should I send her out with my partner and hope they hit it off too?
Would you be okay, if you liked this person, to date them by yourself? Sure, a fantasy/motivation could be the possibility of a compatible threesome but would you also be satisfied with a twosome? If so, it could be healthiest to approach it as that, with no expectations (even if you have hope that it'll be an intimate experience you could some day share with your partner).
If you only
want to be with someone who is into both of you, then yes, anything apart from an upfront approach would be disingenuous. And though that could turn some potential partners off... you'd presumably be left with people who are into that kind of arrangement.