I know Granny said I should cap my age range at 32 for the men I date but I don’t entirely agree and besides, I like to be rebellious. In high school I was always pushing her buttons to test the waters. There was one incident where she bought me a white skirt but told me under no circumstance could I wear it without a slip because it became totally see-through in the sun. Being the brat that I was (am) I wore it the very next day with a bright blue thong underneath. I was strolling down the street feeling outrageously sexy, scandalous, and sixteen when I ran into Granny. She may be fifty years my senior, but the lady is fast and surprisingly strong.
Besides provoking Granny, after my date with the boy toy, I was craving a more developed gentleman. Jeff, a 42 year-old business owner, sounded like a healthy dose of adulthood. He described himself as a “full-grown man”. I pictured facial hair, a mortgage, and an impressive tie collection. Hubba hubba.
He also described himself as a “yoga dude” who likes to get his “Om on”. I found both sayings a little cheesy but I let it slide since he listed many other interests that made him sound versatile, worldly, and manly.
He suggested meeting up at a bar in the west village. Unbeknownst to either of us there are two bars with the same name in the neighborhood. I got to what I thought was the right bar, ordered a drink and began the waiting game. After twenty-five minutes, a finished drink, and an annoying feeling creeping up my spine, I messaged him to find out where he was. When we realized the blunder I tried to hail a cab but there were none in sight so I began speed walking to his destination while I messaged him:
Me: Oh man! Sorry, I’m on my way to you now.
Him: Relax, no worries.
Me: Can’t find a cab. Be there in 20.
Him: Relax. See you soon.
I hate when someone tells me to relax. Maybe it’s because I’m a psychopath, but I feel like someone saying “relax” is a passive aggressive way of making you feel more at edge while they look like the cool cucumber. Relax? I was relaxed. I would have been more relaxed if the full-grown man did the chivalrous thing and suggested coming to meet me since he was the one to pick the venue and never clarified which street it was on. But whatever, I can get my Om on too.
When I finally arrived at the bar, I saw a man sitting by himself. I couldn’t see his face because a cocktail menu obscured it, but judging by the arm full of prayer beads supporting the menu I thought it safe to assume it was Jeff.
“Hey,” I said as I approached the table, “Silly mix up.”
Jeff brought his hands into what looked like prayer position when he nodded hello to me. “Relax, not a problem,” he said. I took a deep breath.
He calmly began telling me about his life and furthermore his theory on life in general, “Do you think the universe is expanding or contracting?” he asked.
He made it clear that he was in touch with himself and very into his spirituality. He told me about his love for rock bands, Asia, and his children. All three of them. The oldest was a fifteen year-old girl.
I like kids a lot. I love kids, but did I really want to be dating a guy who has three? I wouldn’t mind being a second wife but I think I’m too young to settle for that position now.
Although he was a very kind and intellectual man, I’m not the gal that could get into the vinyasa flow with Jeff. Nor do I want to play the role of the evil step-mom next to chilled out Om master dad.
Ugh, Granny 1. Me 0.
I spoke with Granny yesterday to get the scoop on her date plans for this afternoon. “The bastard hasn’t called,” she huffed. “That’s fine with me because I’m busy, very busy,” she insisted. She once told me that if a man is too “busy” to see me that I needed to make myself twice as busy.
Later in the day she finally heard from him, she left me a voicemail recounting their conversation. “He was sick, home with a cold,” she began in a mocking tone. “He’s such a whiney man. He went away for the weekend and it was cold so he caught a cold,” she said, exaggerating the “old” in “cold”.
“He says, ‘Oh my God, Oh my God!’ I didn’t know what was going to happen,” she giggled. “Then he squeals, ‘I’m gonna sneeze!’” She burst out into a fit of laughter. “What would happen if it was really an ohmygod moment?”
“He’s such a baby and a whiner,” she complained, “He’s very sick, he’s telling me about all of his illnesses. All of them.” You’d think that by 87 a man would have learned that women aren’t interested in hearing them whine and list their weaknesses.
“I obviously don’t want to meet him, but he cancelled it anyway,” she told me. “I’m very busy now. Very, very busy.”
I wonder if his cold was really cold feet. The man has a sick wife; maybe he decided that his conscious couldn’t handle a flirtation with infidelity. As Granny always tells me, “You don’t know what you don’t know.”
LISTEN TO HER VOICEMAIL: voicemail.mp3
“I think you should call me when you can because I’d like to share with you something that’s going to shock you,” Granny began in an eerie tone in the voicemail she left me this morning. “Eh, I’ll tell ya right now,” she’s never been good at maintaining suspense. “He’s married.”
She had a phone date with a man from JDate last night; turns out the old bugger’s already got himself a lady. Sadly his wife has Alzheimer’s, which he confessed to Granny after their hour-long chat. This is one of those situations where as an older person the issues are more complex and the baggage more profound. If the situations were reversed and a man was telling me he had a sick partner I’d immediately dismiss him as an option then swiftly kick him in the balls.
“How beautifully honest of you,” she told him. “If you think I’m being sarcastic, I’m not. I appreciate that you’re telling the truth.”
“If you don’t want to meet me now that you know that I understand,” he said.
“I don’t have a problem at all,” she told him. “I’m not looking to get married.” Granny’s had her own complicated romantic history, which gives her more empathy to untraditional relationships and a looser view on marriage.
She was frank, “I’m pretty much here to eat when I get hungry, sleep when I get tired, and breathe my own air in my own space.”
I like that they are starting out with such brutal honesty about where they’re coming from and where they’re expectations lie. I doubt that their relationship will develop into something romantic, but who knows. They do have a date set for later in the week….
After getting the heavy stuff off her chest she was ready to gossip about what really mattered to her, “He’s old, the oldest that have ever admit to his age. He’s admitting to 87, that’s pushing 90,” she whined. “Oh my God, you’re talking about going out with a 22 year-old? Do you think in my mind I’d ever go out with a 87 year old? Ten years older than me? Unbelievable.” The lady is young at heart.
LISTEN TO HER VOICEMAIL: voicemail.mp3
I checked in with Granny after my date with Chad to get her thoughts on younger men. “He’s gotta be mature, have a good head on his shoulders, be fun, someone you can enjoy the pleasure of their company,” she advised. Based off our date, Chad was 0-4.
I asked what age range she thought was appropriate for me. “Don’t date older than 32,” she warned.
“What if I’m just fooling around?” I pried.
“I don’t care how old they are as long as they’re of age so you’re not going to jail,” she casually advised. “18? 19? What’s legal?”
I was aware that Granny was open-minded but I didn’t expect her to be chill with me hooking up with a high school senior. When she heard the shock in my voice she said, “Listen, I don’t care if you’re just having a good time with them. This isn’t serious dating. This is, ‘Let’s take a walk and have some fun.’”
I feel pretty confident I won’t be taking any walks with teenage boys… but never say never. Chad was emotionally too young for me which Granny boiled down to my threatening presence. “No guy wants to be threatened by a woman because if he’s feeling threatened then he’s not going to be nice to this woman or he wants a mommy. In any event, you don’t want that kind of relationship.” I’m not fit to be a mommy but I do enjoy the idea that I am threatening men in this city.
I turned the table on Granny and asked her what she thought was age appropriate for her. “I’m a spring chicken to a 96 year old,” she seriously stated. “That’s one of the differences between dating for you and me.” Granny claims that in her online dating experience she rarely catches the attention of men her age let alone younger. I love being a woman but it bums me out that as a man the older you get the larger the age range of women you can date while for women it’s the opposite. I might need to reconsider my stance on younger men while the option is still on the table…
LISTEN TO OUR CONVO: convo.mp3
Ever since puberty struck I’ve had a thing for older men. It started with Mike Catrambone; he was the first guy I locked lips with. It didn’t matter that I was four inches taller than him or that his braces gave him a slight lisp, he was fourteen and I was twelve and that was all I needed to know to swap spit with him under the docks at sleep away camp.
After little Michael, the streak continued. I like mature men, men with experience, men with some wisdom that can inspire me. In all my dating years I have never been out with a guy my age and certainly had never considered going out with anyone younger. This was until a very sexy, talented friend of mine gushed to me about how much she was enjoying her boy toy. “I get to be the boss,” she bragged. “Everywhere except in the bedroom.”
This arrangement appealed to me. I’m fairly controlling, I wouldn’t mind having a young lad at my beck and call. My feet are not going to massage themselves. I’m 25; I think it’s safe to say I have a few years left until dating a younger man would qualify me as a cougar.
When Chad messaged me on OKCupid I saw he was a handsome young chap, his brown eyes struck me as murky pools filled with profound mystery and maturity. He was wearing nicely tailored suits in three out of four of his pictures. Menswear gets me hot.
His profile wasn’t showy or heavy on details but it still intrigued me. He wrote that he was “an Englishman living in New York”. Well dressed with an accent? Somebody slap me.
When I noticed that he was 22 I was bummed and ready to click onwards to the next man but then I thought back to my friend and reconsidered. Why not? That’s the beauty of online dating; you have nothing to lose by trying out men who typically wouldn’t fit your mold.
I agreed to meet Chad for a drink. The bar was crowded when I arrived so I messaged him, “I’m the girl in the blue striped shirt.” When I looked up I saw a young boy with a Justin Beiber inspired hair-do scanning the bar. I looked to my left and right and noticed there were four other girls wearing blue striped shirts. The nautical look is taking over.
I let him sweat it for a moment, his cheeks turning a rosy shade of red. I finally raised my hand and he awkwardly rushed over in a flustered Michael Cera-style, his cheeks reddening with every step. He didn’t look like the confident suit-wearing fella from his pictures; he looked like the missing member to a boy band.
When we started chatting I immediately noticed there was no hint of an accent coming from the man-child. When I brought it up he broke out into a fit of nervous laughter and explained that he moved to the states with his family when he was six. I thought it was unfair of him to refer to himself as an “Englishman” in his profile but I let it slide because he was clearly on edge.
“What are you doing in the city?” I asked.
This brought on another series of giggles, “I just graduated college,” he said, looking away as if he didn’t want to embarrass me, the older woman.
Every question I asked him evoked bashful and embarrassed responses. I was doing the regular: “Where you from? Where do you hang out? What neighborhood do you live in?…” But by the reactions he was giving me an onlooker would have thought I was asking him how many times a day he masturbates.
My presence was obviously making him uncomfortable. I think I must have come off too dominating. Will, my HowAboutWe date, told me I had that habit. “You’re very self-assured, I think it’s probably intimidating to the guys you’re meeting from the sites,” he warned me.
When we finished our drinks I asked him if he had any big weekend plans. “Probably gonna get some forties and drink them in Fort Greene Park with my bros,” he said.
The kid can wear a suit and take an excellent self-portrait. I’m sure he’ll have a bunch of fun in the city but I think the window for me drinking forties in the park ended years ago. I definitely didn’t want to be this guy’s boss.
The cuddler was not going to crawl solo under his sheets so fast. After Granny’s date with Mike, she received several calls from him throughout the week. That’s the problem with giving your phone number to online daters; often they’re not afraid to use it.
“You know,” she told me, “I was angrier the morning after then the night before when I realized what nerve he had, what chutzpah. Ya know? It pissed me off.” He was barking up the wrong tree, Granny is not the type of gal that’s going to give it up to an old sack of bones after a cheap date. “He has no patience,” she said, “I’m not jumping into bed with him.”
He tried to convince her that although he was Catholic, he had been with Jewish women before. I didn’t understand why this fact was at all important. I think it’s safe to say that most singles in my generation sleep with people of all races, religions, colors, and background.
“So he has a Jewish fetish?” I asked.
“He likes the Jewish girls, that’s what he was trying to let me know,” she huffed.
“So? Jewish girls are hot,” I reminded her.
“JEWISH GIRLS ARE HOT,” she screamed back at me, “But he was not.”
LISTEN TO OUR CHAT: convo.mp3
Granny is not a fan of Mark. When I told her about his red eyes and lengthy bathroom break she immediately concluded, “He did drugs in the bathroom.” She’s never been one to hesitate about jumping to the most scandalous option.
When I revealed that he asked me to avoid eye contact she gasped in disbelief, “Listen to me, when something strange like that happens it happens because he’s a strange fellow.” Although Mark was definitely an oddball I felt Granny was being a little quick to judge. I reminded her of the incident when he tooth fell out on her date with Prune Face. He didn’t run up and leave because she had an embarrassing accident. Instead he soothed her self-conscious nerves and made her feel at ease.
“Yeah, and then he never called me again,” she reminded me.
I stuck to my guns, maintaining that the considerate thing to do was stick it out and let the guy get his story off his chest. “This is the difference, I didn’t know my tooth was going to fall out… He knew he had an issue and he still came to meet you.” Sometimes I just like to argue with Granny for the sake of arguing. Clearly she was right, but part of me will always be the bratty middle granddaughter.
“I hope you didn’t touch him,” she warned. “You don’t know what you don’t know. Besides that, he was too short. He sounds like a weirdo.”
LISTEN TO OUR CONVERSATION: convo.mp3
Mark’s profile was wordy. Possibly the lengthiest of any I have seen so far. We’re talking detail upon detail about his life, character, profession and goals. Typically overly thorough profiles are a turn-off for me but he had an eloquent writing style and included many interesting reveals. For instance, he mentioned that he had five sisters. A man who grew up with a boatload of gals has got to be a unique human being. I had two; between the three of us we had enough estrogen to kill a horse. I was curious to see how Mark turned out.
When he messaged me he didn’t send the quick “let’s grab a drink”, rather he wrote a manifesto about a fedora he recently purchased. “I look terribly handsome in this hat,” he confessed.
I’m a sucker for a good hat and a man with talented writing chops so I wrote back, “I wouldn’t mind having a drink with you and your fedora.” He explained in his next message that fedoras don’t drink and neither does he so we settled on an afternoon tea. Although I didn’t exactly see it in his pictures, he described his looks as “a cross between a vampire and Johnny Depp”. I’m addicted to True Blood and I’m a woman with a pulse so clearly I was intrigued.
I got to the coffee shop on time, ordered a tea, and took a seat. After waiting ten minutes I saw a tiny man with a fedora come in, he didn’t resemble Johnny Depp but I got what he meant by vampire when he removed his hat and revealed his pale complexion and red eyes. Yes, red eyes. The whites of his eyes were blood red.
I tried not to appear too shocked, but it was a condition that deserved an explanation. We quickly introduced ourselves, he said that he must have allergies or an infection but promised it wasn’t that he was “higher than Snoop Dogg”. I made eye contact, which is the normal thing to do, I didn’t want him to feel uncomfortable about his condition but apparently my manners backfired, “Would you mind not looking at me directly?” he asked. “I’m feeling very self-conscious about my eyes.” I offered him up my sunglasses but he declined.
“You’re disarmingly beautiful,” he told me. Before I could respond he excused himself to the bathroom where he spent at least ten minutes. I considered getting up and leaving but he gave me the best compliment of my day so I stuck around. I looked at the cute college girl beside me who was politely pretending to type away at her computer but was very clearly eavesdropping on my encounter. She was doing a terrific job of stifling a laugh.
When Mark finally returned he jumped right in to telling me his life story. The whole story. He started at age twelve and worked up to his current position in life at thirty. The only break he took was to play with a dog that came in. He got on his hands and knees in the café and scratched the golden retriever’s belly and baby-talked to him. Me, the owner, the dog, and the college student all exchanged “WTF?” looks.
His story was highly emotional, he began with a rough up bringing, a girlfriend who got him evicted, a failed attempt at college, and it ended with him getting fired from his hospitality job yesterday. I wasn’t sure if the tears he was wiping from his eyes were from the hardships he faced or the puss from his infection.
It was a lot of information. Too much information. I was deep in TMI city. I’m all for being in touch with yourself and your emotions but on our first coffee date I didn’t need to know most of the goods he was dishing out. Not to say he wasn’t interesting, he certainly was but some of the things he told me would have taken me months of bonding to share with someone, and as we know, I’m an open-deck of cards as is. I like a man with sisters but maybe he had too many sisters.
He sent me a message after our date, in his manifesto style, from the waiting room of the doctor’s office. Besides the eye infection it seems he’s also caught a bout of love fever for yours truly. If you take out the time that I waited for him, our date lasted about thirty minutes, in those thirty minutes I probably talked for five of them, yet he wrote me a two page letter about how “rad” I am and the true “connection” he felt. Mark was a nice guy with a cool fedora but he is certainly not my cup of tea.
Before her date yesterday Granny called me in a huff. “Kid, I got a speeding ticket, those bastard cops came out of nowhere.” This is her second ticket this month. Granny is a crazy driver. I don’t mean crazy for an old person, I mean generally insane on the road. The lady cuts people off, zips through red lights, and takes pleasure in yelling creative profanities out her window. One time I was driving with her and a man cut in front of her, Granny followed him on his tail for three lights until she finally caught up to him, signaled to roll down his window, then said, “What are you sick?” he shook his head confused, “You gotta be sick to pull a move like that.” Then she floored it and speeded away. Although she is maniac behind the wheel I still felt sorry for her. It’s a true bummer to get a ticket, especially before a date.
She called Mike to let him know she was going to be late and tightly wound. “Don’t worry,” he said in a suspiciously soothing tone, “We’re going to have a glass of wine and get you nice and relaxed.” It seemed like a sweet remark, not a precursor of some sketchy old fart behavior.
“I’ll be the handsome, stylish man in the tan slacks and navy shirt,” he told her.
“He looked like he walked out a Sears catalogue from 1992,” she said. “At least he was clean, but handsome? Stylish? I don’t think so.” Apparently he arrived an hour before her to scope out the spot. Granny suspected that he wanted to check the prices on the menu, “That’s what they do,” she grunted, “They figure out how much they’re gonna have to spend.”
She ordered a beet salad, she explained to me several times that it was only six dollars which I agreed was rather cheap for a beet salad. Mike disagreed, “Ya could buy three bunches of beets for six dollars,” he said. She also ordered a hamburger, she sounded out every syllable of the word for me to emphasize how modest she was being in her choice of food.
When the check came Mike pushed it into the middle of the table. “I ignored it,” she said, “I said nothing, did nothing, and pretended I never saw it.” Mike invited her to dinner, she had suggested just drinks but he pushed for dinner therefore I’m on Granny’s team; it shouldn’t have even been a question of whether or not he was going to pay.
All of this we could have worked through, but then she dropped the bomb, “You ready? At the end of the meal, he leans in and says ‘Do you like to cuddle?’ Oy vey smear,” she huffed, “It was like a hatchet falling over my head.” I was now pissed at Mike, if a guy brought up cuddling to me on a first date I’d probably be creeped out, but to my Granny? No sir.
“Oooo yes, I like to cuddle,” she purred to him, “But not until I sincerely feel like cuddling when I know the person for a little while.”
“He had in mind to go to bed with me and do nothing because he can’t have sex, I’m sure of it,” she told me. “All he wants to do is feel me up and get his jollies that way. No way, not doing it. I know where it’s going and it’s not going there.” Amen.
After I listened to her message I gave her a call back to get more of a scoop and ask her how she handled herself and the situation. “I didn’t know what the hell to do because that’s never happened before, who the hell acts that way?” she asked.
She handled it like a classy gal, turning the inappropriate question in on him to make him feel uncomfortable, a technique I like to practice. “What’s your idea of cuddling?” she asked him. “He says to me, ‘You know what I mean.’ I said if I did I wouldn’t ask you, what do you mean by cuddling and I’ll tell you whether or not I like it.” I love that she put him in the hot seat!
“You know hugging, kissing, rubbing each other nicely,” he told her.
“So you want a massage?” she asked him. He nodded eagerly. “I’m not offering, I just wanted to get a clear definition of a cuddle. But it sounds like a romantic massage to me. Did you think that in meeting me that would be involved in tonight?” she asked him.
Mike tried to explain himself but she cut him off, “I don’t know you, I barely know anything about you and I would never consider any of that until I got to know you over several occasions of getting together with a lot of nice dinners.” She added the nice dinners part because she knew he was cheap and it would scare him off.
She got up to leave and he insisted walking her to her car, “He put his arm around me and tried to get a grope. I said, ‘You gotta be kidding me.’”
He then readjusted his arms and tried to get a squeeze at her tush, then he planted a surprise kiss smack on her lips and said, “Gotcha!”
“Never again with this man,” she warned me.
Between the date and the speeding ticket I was feeling really bad for my Granny. I called her back to check in on her. I expected her to sound more downtrodden but instead she was giggling, “I took my rage out on AT&T, I told them off just now. God, that felt good,” she said.
I asked her if she was feeling down about the whole Mike thing, “Honey, if he were the first online guy I went out with he might have scared me off but I’m a pro now.” She sure is.
LISTEN TO GRANNY’S POST-DATE VOICEMAIL: granny_voicemail.mp3
Granny has taken to talking about herself in third person as if she were referring to a well-behaved Shih Tzu deserving of a fancy treat. She left me a voicemail, updating me on her latest telephone courtier, Mike. “He’s either a Jew or very Brooklyn Irish Catholic. He has a very heavy New York Jewish accent,” she said in her own stereotypical New York Jewish accent.
She delivered incredible visuals from their phonecall that activated four of the five senses, “I think this man has emphysema, he coughed the entire time. It sounds wet, like if you were near him he’d be spitting mucus all over you.” To balance out her criticisms she mentioned that Mike has no problems with his eyes and drives in the dark, these are qualities that an older gal admires in a man.
Months ago when we started this online dating journey, Granny was more than hesitant about putting her information out there on the internet, she was adamant that she didn’t want any online men to have access to her home number because she was sure they were going to try and steal her. It took a full week for me to convince her that using an alter ego was not the way to get online dates. When Mike left her a message on her cell phone after she gave him her number through Match, she called back on her home phone by accident and left him a message, then he called her back on her home phone because he saw the number in his caller ID. I was relieved to hear she’s loosened up her policy, “I don’t care anymore. These men are on deaths door,” she said, “They’re not going to do anything to me, look me up, come visit me, get nuts or any crap.”
Although she loves to knock them down I know part of her thinks this one could be an interesting match. She told him to give her a call sometime, “I made it loose,” she told me. “If he starts spitting juice on me it’s not happening.”
LISTEN TO GRANNY’S VOICEMAIL: granny voicemail.mp3