Mermaid Problem

The Mermaid Problem is an observation occasionally mentioned in literature, concerning the difficulty of having [...] intercourse with a mermaid.

Although mermaids are commonly depicted as beautiful, variably [...], and enticing, a man attempting hypothetical [...] with one would be thwarted by the typical portrayal of the creature: a fish from the waist down, with no vagina. Some fiction, aware of the long running question, deliberately avoids the question for humorous effect.
More GeneRally, it can also be a joking reference to the unusual [...] interest many non-human characters seem to have with humans in fantasy or science fiction, and potential physical issues therein.

Theoretically a mermaid would reproduce as most aquatic animals do, by external fertilization, requiring a human male to deposit his seed underwater onto her eggs. (The confusion is further compounded by the fact that mermaids are usually depicted with a navel, which would suggest placental vivipary rather than ovipary.) In some fantasy erotica, however, this situation is sometimes rectified by portraying mermaids as having genitalia more similar to dolphins than fish, or having the ability to change into human form.

Interestingly this was not always an issue. In the past it was not uncommon for a mermaid to be portrayed as having a split tail, with a vagina located (or merely inferred to be) between The Two parts. The well-known Starbucks logo is one example of this. In the original version the mermaid is shown spreading her tail apart up to her head. While this has been cropped out, and the drawing in general slightly ReWorked over the years, her tails are still visible around the edges.

Examples of Humor

In the Futurama episode "The Deep South", Fry befriends and romances a mermaid from the lost sunken city of Atlanta. He later has his hopes dashed after attempting [...] with a very confused partner, who expected intercourse more typical of a fish. He laments, "Why couldn't she have been the other kind of mermaid, with the fish part on top, and the lady part on the bottom?"

In the Red Dwarf episode "Better than Life" , the Cat solves the same problem while playing a virtual reality game when he dates a mermaid with exactly that physical description. When ship's mainframe Holly notes "Somehow I'd imagined she'd be a woman on the top and a fish on the bottom," the Cat replies "No, that's the stupid way around!" Coincidentally, Craig Charles (who plays the character David Lister on Red Dwarf) also plays the title role in the Channel 4 sitcom Captain Butler, who is enticed to wed a mermaid but reconsiders as he finds out he has to be transformed into a half-man-half-fish hybrid with the "fish half on top".

The cover of The Hard and the Easy by Great Big Sea features a "reverse mermaid" with an enticing pair of crossed legs in high heels, with the upper body of a fish. The back artwork shows a regular mermaid.

In an episode of "Saturday Night Live", a man crash landed on an island and met a mermaid, played by host Reese Witherspoon. He wanted to know who her parents were and was confused AbOUT her being half woman half fish. The mermaid then introduced her father who sang about how he has "had [...] with a lot of things".

The poet/songwriter Shel Silverstein made this problem the centerpiece of his humorous song The Mermaid, about a sailor who is warned against falling in love with a mermaid, which he proceeds to do. The lyrics read in part, "From her head to her waist she was my taste but the bottom part was a fish." The song ends with the sailor dejected after being dumped by his new mermaid love, but finding consolation when "her sister swam on by, and set my heart awhirl / For her upper part was an ugly old fish but the bottom part was girl!"

The webcomic Penny Arcade makes a joke on this subject as well as Gabe remembers his younger "Undersea adventures" or attempts in any case. He asks Disney's Little Mermaid "Where the hell is your vagina?"

In an Oscar Wilde short story, a man falls in love with a mermaid and goes to live with her under the sea. After wisdom and wealth fail to entice him back to land, he returns to see the beautiful legs of a dancing girl.

A simple joke goes along the lines of a fisherman catching a mermaid, but deciding to let her go. His assistant asks "Why?" to which the fisherman replies, "How?"

P.C Cast wrote of this particular problem in her novel Goddess of the Sea from her Goddess Summoning series. Within, the mermaid in question does have [...] with a merman, though the [...] on her part is never fully explained of 'how'. It is insinuated only that she has a slit within her tail, as does the male where the penis is located.

In Piers Anthony's novel "Mercycle", a race of merfolk who are the genetically modified descendants of normal humans appear. Although they appear to have a standard tail, the tail is actually divided in two in a structure closely based on human legs.