If you’ve been in the dating world for any span of time, I am willing to bet that you have at least one story about a bad dating experience. There have been a few doozies in my dating life, but one in particular was particularly aggravating. I’ve gotten so many laughs from relaying the story about Max that I figured my subscribers would also get a chuckle out of it.

I met Max (and yes, that was his real name) at a Halloween party in 2009 at the Skirball Center on Sepulveda Blvd. While I was at the party, a very nondescript man who was not at all my type approached me, began talking to me, and followed me around. You guessed it, this was Max. He refused to leave my side, cockblocked a number of men who were my type, and just annoyed me to no end. When I decided to leave the party, he hounded me for my phone number, and for some utterly stupid reason, I gave it to him.

Max called me the next day, asking if I was free, to which I replied that I was watching Sunday NFL Football with my roommates. Without hesitation, Max invited himself over, and because I was so distracted by the activity in the house, I relented and gave him my address. When Max showed up at my place, he was empty handed, and promptly asked if we had beer or some other libation he could enjoy. I opened up a bottle of sake and poured two glasses. About 30 minutes after Max showed up, my two roommates stated that they were planning to put some burgers and chicken on the grill, and invited Max and me to join them in consuming the food. Once the food was cooked, the four of us sat in front of the TV, eating, drinking, and watching the game. A big smile broke on Max’s face, and he said, “Wow, this is awesome! I’m getting free food, free booze, and I’m watching football!” which made me cringe and also triggered concerned expressions on both my roommates’ faces.

Once the afternoon game was over, I told Max I had an early day the next day, and thanked him for coming over. Max stated that he would make it up to me the following week by taking me to dinner, to which I reluctantly agreed. Two days later, Max called me and we made plans to meet at a restaurant called Firefly in Studio City that Friday. For those of you who don’t know the restaurant, here is a portion of the current (2022) dinner menu:

Fried heritage chicken with mashed potatoes & gravy, horseradish slaw
and a damn fine buttermilk biscuit (or just as fine GF cornbread for the intolerant)   29 

Potato kugel with king trumpet mushrooms, roasted carrots, tofu creamed spinach and truffled demi   28
Red chile braised pork with crinkly sweet potatoes, collard greens, crispy mushrooms and pepita–cilantro salsa   30

 Zucchini, corn and poblano enchiladas verdes with black beans, romaine, pickled red onions and cashew crema   27

 Moqueca Baiana of rockfish, mussels and scallops with watercress–watermelon radish salad and jasmine rice   31

 Dijon crusted ocean trout filet with seared asparagus, quinoa–pine nut pilaf and sauce gribiche   33

 Baked mac ‘n cheese with cheddar, gruyere and parmesan bread crumbs   12

On Friday, Max and I met at the restaurant and were seated at a lovely al fresco table. The waiter brought menus and took our drink orders, which consisted of two similar mixed drinks on the rocks. Max perused the menu for several minutes, then looked over at me with a dissatisfied facial gesture. I asked him what was wrong, to which he replied, “I just don’t see anything that is grabbing me, ya know? I think I want to see if they can make a burger for me.” Since I wanted to be a good sport, I told him that if the chef was willing to accommodate his request, I would also have a burger. Well, Max got his wish, and we ordered burgers. We also ordered a second round of drinks.

The burgers were delicious, and our conversation flowed better than I thought it would, but since I felt no romantic spark with Max, I just wanted to get through the date without any awkwardness. Then the waiter placed the bill on the table while Max and I were talking about something that made us both laugh. While still laughing, Max picked up the bill, glanced at it, scowled, threw the bill onto the table, and remarked, “Oh, I can’t pay this!” I picked up the bill and saw that the total was $75, and because I wanted to be accommodating, I suggested that we split the bill, to which he agreed.

Two minutes later, Max scowled (this time at me), said “Wait a minute!”, and grabbed the bill. He studied it for a minute, then remarked, “The drink you ordered is $1 more than mine, and you had two of them, which means you owe $2 more than me.” I just sat there, dumbfounded. Was this guy really that cheap? I was so disgusted and so intent on getting out of that restaurant that I told him, “Don’t worry about it, I’ll pay the whole thing.” I proceeded to pay the entire bill plus tip, because Max didn’t even offer to leave the tip.

When we walked to the valet area to pick up our cars, Max said, “I’ll pay your valet fee if you let me come over” to which I replied, “No thank you, keep your $5.” Needless to say, there was no third date with Max, but he continued to call me, begging me to take him with me to Preview Night at the L.A. Auto Show. I had purchased two tickets (at $100 a pop), and mistakenly mentioned that I was going to the event and was waiting to hear back from a friend who said he wanted to join me. Max truly believed that I would have been willing to take him, on MY dime, to the event. I asked him to please stop calling me, and when he refused to leave me alone, I blocked his number.

I’d love to hear about your nightmare dating stories, so please share in the comments!