“So, what do you think?”

I looked down at the package he had placed on the table and considered my response.

1. I could be honest. This would be the best result overall, but would mean he got the full wrath of my judgement
2. I could lie. This would be immoral, but also ensure his feelings did not get hurt
3. I could withhold my opinion. This would give him the opportunity to show off his purchase and receive the feedback he needed

I chose the latter.

“They’re Y-fronts” I remarked nonchalantly, wondering if he would realise through my tone of voice, how much of a mistake I thought he had made with his pant-buying.

“Yes,” he said excitedly, “nice aren’t they?”

“Well, they’re Y-fronts” I stated, thinking that perhaps if I just repeated myself, that would eliminate any possibility of my being rude to him absentmindedly.

He picked up the packet of (3 x) white pants and handed them to me. “Have a look. What do you reckon?”

I held the package in my hand and an image of him wearing Y-fronts suddenly entered my head. Given that I normally like the thought of men in pants (especially if I have the chance to rip them off), it was not without some irony that I was trying to empty my mind of this particular thought. But he was my mate and I really didn't want to think of him in that way - especially with Y-fronts on.

I wondered how I could respond in the least offensive manner. Perhaps if I came up with a question, it would deflect attention away from my negative opinion and onto his enthusiasm instead.

“So, do you actually use the hole in the front then?” I asked, prodding the pants through the plastic wrapping. “Does it make for easy access?”

I looked up at him and from his blushing, suddenly realised the inappropriateness of my question. Another image of him in pants appeared in my head.

He stammered a little. “Well, yes, of course. I mean…”

“Right” I interrupted, fully aware neither of us really wanted to be debating the merits of him being able to stick his cock through a front opening – of any sort. “So they must be comfortable I imagine?”

“Ooh yes, really comfy” he said, sounding relieved I had moved the debate on. “What size are you?”

“Me? I’m a medium. Why?”

“I reckon a man’s small would fit you” he said, adding “and I have a pack of them at home.”

“But they’re boys’ pants!” I exclaimed, still trying to get the image of him modelling the Y-fronts out of my head. “I’m a girl!” And no way would I wear anything like that.

“You could look like Sarah Jessica Parker!” he said, excitedly.

“What?”

“She wore her boyfriend’s Y-fronts in Sex and the City. You could definitely get away with it like she did. They’d look great on you. I’ll give you the spare pack I’ve got” he added.

Oh great. A bloke is reciting an episode of SATC to me. And he’s not gay. And he thinks Y-fronts look good on women too. Clearly he has no taste. Oh god how do I get out of this without totally offending him?

I pondered for a moment and then came up with the best answer I could. Leaning over to him, I gently placed my hand on his and in my most seductive Girl voice said,

“Why would a woman want to wear pants made for boys when there are the silkiest thongs, the laciest French knickers and the sheerest tie-string panties to choose from to look sexy in?”

He looked at me for a moment, thinking, and then said, somewhat triumphantly,

“Fair enough. But what about to sleep in then, ‘eh?!!”

I smiled at him. “My dear, the joy of underwear is to take it off – preferably in front of someone else. There is never a need to wear pants to bed. At least, not in my bed.”

He laughed. “Ok, yeah, you’re right, good point.”

“Save them for your next girlfriend” I said, as he hurriedly put the packet of Y-fronts away.

But we clearly have some work to do if you're determined to stick with the Y-fronts until then.