My mom asked me for advice when she was juggling two boyfriends. One was technically her ex (she kind-of dumped him). I was all of 18 and haven't been in a relationship yet. My answer was a simple "Why the fuck are you asking me?"
The most awkward would be my grandmother, and it was less a conversation than a lecture. She gave me an hour long lecture about how I shouldn't marry a blond (because "you don't want used products, and all blonds have been used before"). She also ruled out redheads, blacks, Indians (as in the girls from India, though I think she would have included the natives if she had known of their existence), Arabic (and Muslims in general) and Latinos. Which basically left me with Brunets and East Asians. She then followed that by saying that brunets with white skin are most likely sluts, and that all Southeast Asians (Vietnam, Thailand, etc) are whores. All of this basically narrows down her approval range to Chinese, Japanese, Korean, and Taiwanese girls.
Awkward because my grandmother is talking to me about my potential wife (and classifying about 85% of all females as sluts, whores, or just dirty women). Hilarious because there was so much racial prejudice it was AWESOME!