As a waiter/waitress what is the weirdest thing you have been asked?

Back in my college days, I was like many college students; Broke, hungry and looking for a way to get through college. One of my friends worked at a local surf and turf restaurant and asked me if I would be interested in a wait job. I jumped at the chance.

This restaurant was nothing special but did have a unique attraction. It had an all you can eat salad bar with your meal and all the beer and sangria you could drink. At first, I started out working Mondays through Thursdays. The Friday through Sunday shifts were taken by the more senior wait staff because there were always bigger crowds and better tips. I made decent tips but nothing like the weekend staff. One week the manager asked me if I could work Fri.-Sun. because one of the other waiters had quit. I jumped at the chance again.

Friday night came and there was a line at the door. I knew this was going to be a good night. Two ladies were seated at one of my tables. I approached and asked what they would like to drink. One lady said, “My name is Cheryl”, so I introduced myself. Then she said, “this is my friend Sue” (not real names). I extended my hand to Sue and said, “nice to meet you”. Cheryl said, “I would like a Beefeater martini extra dry and Sue will have a margarita without salt”. I got their drinks and asked for their dinner order. Cheryl looked at me and said, “I’ll have the usual and so will Sue”. I had no idea what their usual was and said as much. Cheryl said, “the kitchen knows, just tell them it is me”.

I went to the kitchen and told them Cheryl and Sue were here and wanted their usual. The cook did not even blink an eye and put two filets on the grill and put two lobster tails under the broiler. In a few minutes, I delivered their food and they already had their salads.

I paid pretty close attention to them and gave them extra special service because it was obvious they were regulars. They finished, left a very nice tip and I saw them speaking with the manager as they were leaving. Seems they had asked for me to be their new server when they came to dine.

Sure enough, the next Thursday night they entered and were waiting in line to be seated. When I first saw them enter I went straight to the bar and ordered their drinks. As they were being shown to one of my tables, I was on my way with their drinks. As soon as they sat down, their drinks were being placed in front of them. I looked at them and said, “the usual for dinner”? They just nodded.

This became a regular tradition for months. It became obvious they were a couple in an era when gays and lesbians were not so open as they are today but it did not matter to me. They were always very nice and left a 20%–30% tip when 10%-15% was the norm.

One Thursday, they came in with another couple. As always, their drinks were at the table when they arrived but I needed to take the drink orders from the other couple. The other couple were obviously impressed at the service Cheryl and Sue were getting and just said they would have sangria with their dinner.

Their food was ordered and served. When they finished, one of their friends asked me for a pack of Marlboro cigarettes (in an era when smoking in a restaurant was still allowed). We did not sell cigarettes but had a convenience store next door so out I went in my apron, bought her cigarettes and returned them to her at the table. When I presented the bill, Cheryl asked me where the charge was for the cigarettes. I told her I had just gone next door and purchased them since we did not sell cigarettes. Her friends could not believe it and the one I got the cigarettes for gave me more than twice what they had cost.

Then, one Thursday night Cheryl asked me if I might be available to work at a party she was giving for one of her friends. She told me she would pay me double per hour what I was making plus a nice tip. I told her I would be delighted and she gave me directions to her house.

I arrived well ahead of her guests. To say I was impressed with her house would be an understatement. Two storey, colonial, brick with wrap around porch on about acre or land. This lady had money or had inherited it!

She showed me around her kitchen and gave me instructions for the evening. Make drinks for all of her guests and deliver food from the kitchen to the table. (She had a cook in the kitchen). All of her guests were female and many were couples. They were also dressed to the nines in long evening gowns and impressive jewelry. Turned out to be a rather lavish dinner party with country club place settings, and seven course meal. I served the food and removed plates and dinnerware between each course. I also kept their wine and water glasses full. All were extremely nice and many asked me about college and how much longer I had in school. In fact, when I told them I was still a junior and had a year left, they all sort of made a show of light applause. Had me very curious but I just went about my business.

At the end of the evening, Cheryl told me what an impressive job I had done and her friends were very pleased with their evening. True to her word, she gave me double my hourly rate at the restaurant plus a $200.00 tip. I almost fell over in disbelief. That was about what I made in two weeks worth of tips working at the restaurant. It made my day, my week and my month.

Then she commented, “you obviously know we are all lesbians but have never said a word about it”. I responded that their sexual preference was not important to me so long as they were happy with my work. “Oh, we are very happy with your work. You see, we do these dinner parties on a monthly basis because there are not a lot of places we can go to in public as a group” she added. “We would like for you to work our monthly parties if you are interested” she said somewhat matter of factly. Again, I jumped at the chance.

It became a monthly event at different ladies homes, each one trying to outdo the previous month’s event. There was always lots of leftover food which happily made its way to my fridge and would sustain me for at least a week. Many times, the partially empty bottles of liquor and wine would leave with me also as many did not want their families to see liquor in their homes.

It blossomed from there to doing handyman work at their homes, running errands and in some cases even doing their grocery shopping. Most of the ladies held prominent positions as doctors, lawyers, architects, realtors and other professions. I became their go-to guy for almost anything they needed. A couple of them turned out to be bi and there were even some romantic encounters that were hush, hush amongst the group.

When I graduated, I had saved enough money to buy a new (used) car and paid cash for it. They threw me a big graduation party and loaded me up with all kinds of presents including new clothes, items for my new full time job I had landed with a big company in a different city and lots of cash.

I know this is a long story but it goes to show that acceptance in a time when acceptance was not in vogue paid off handsomely. Perhaps a little more acceptance in today’s society could pay off as well!