Let's break this song down: it is about Dean trying to get laid. How do I know? Listen to the lyrics. It's sung as a conversation between two young people who are courting, with the cheery 1950s female backup singers (probably all wearing garter belts and silk stockings) playing the role of the lady to Dean's bachelor. In the first verse, the female states twice, I've got to leave. She invokes the maternal worry & paternal threat to keep Dean at bay. What keeps her there? Maybe she'll have "just a half a drink more". Dean obliges. One of the very next lines is "Say, what's in this drink?". Obviously, Dean is trying hard to get her drunk to take advantage of her '50s style. The whole time Dean is coming up with comebacks to all of her excuses for leaving, and complimenting her at every turn. This is a way of picking up women known as the "Rule of 3". Three drinks or three compliments will usually get you to leave with a lady. The key to this whole verse is the line that the lady sings "at least I'm going to say that I tried", which implies that she is going to give in and get down (score one for Dean!) and knows he'll talk about it around town. Jerk.
Now let's take a moment to mention that in the crappy Rod Stewart-Dolly Parton remake from a couple years ago, they removed the half a drink more line. What? Two adults can't talk about how the woman drank a bit and made a mistake with a man? This is too shocking? Stupid. We've swung so far PC that the pendulum swing back will probably be very nasty.
What's great about the second verse is that this female part mentions three relatives in the second half: sister, brother, and maiden aunt (who is vicious). Who the fuck has a maiden aunt? Was she a school teacher who had to remain single as long as she taught? Is she some old mother hen that cockblocks swinging cats like Dean Martin? She couldn't find a man of her own so she hounds her niece? Ungh. Dean counters this by talking about her delicious lips twice. In the Dean version, the female sings "just a cigarette more", YEAHHHHHHHH! Awesome reference, back when smoking was an adult and supposedly glamourous thing to do. (Of course, the Stewart version does not says cigarette because adults deciding to smoke with their free will is bad). Beautiful touch to the song. Really sets the mind's film reel in motion.
The last verse has the lady asking for a comb, because they got frisky and she doesn't want her hair looking mussed up. I think after the delicious lips and cigarette references, we know why her hair is mussed up. Dean's like, why leave? We can get down again. She mentions the neighbors will talk or even just hint at things to be inferred by others. People were cooler then; now they'd just say "Jenny got drunk & phucked Dean last night, untz". Now, the coolest detail of the song is when Dean is replying to the tomorrow and implied lines he sings "think of my life long sorrow", like her shutting him down would wound him so much (skank), and then the topper "if you caught pneumonia and died". He's throwing the Hail Mary pass here, trying to get her to stay by making her fear death. I'm pretty sure at Brown University, what Dean and this girl do is considered rape.
****I'm a big Dean Martin fan. Smooth voice, smooth style, class, great hair, and smooth with the ladies. Look at the photo I attached in this post. Dean's hugging his girl. Dean's a good guy. He drew her in so tight that he could check out another girl without his main squeeze noticing. He's liked "oh yeah, i got a girl, i'm dependable, women, you can trust me". All the while, he's using that as bait for his lady train. Nice taste Dean, both ladies are foxy.