Shag:

Gwen, because I can't marry her, she's married to Rhys. Who I am sure would be very understanding.
Cliff:

Jack. Work with me on this. He's the one that can't die and will entirely understand my logic. Also, any non-cliff-related plans I may have afterwards are entirely outside the answer of this question ;)
Marry:

Toshiko. Mostly because in comparison to Owen I am a cake-walk, and she's significantly more my type than Ianto.
( The Other Days )

Gwen, because I can't marry her, she's married to Rhys. Who I am sure would be very understanding.
Cliff:

Jack. Work with me on this. He's the one that can't die and will entirely understand my logic. Also, any non-cliff-related plans I may have afterwards are entirely outside the answer of this question ;)
Marry:

Toshiko. Mostly because in comparison to Owen I am a cake-walk, and she's significantly more my type than Ianto.
( The Other Days )