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Archive for the ‘dating’ Category

Entertaining For Now


I had dinner with WM last night at El Five, a tapas restaurant in the Highlands neighborhood. The restaurant has a commanding view of downtown, which we enjoyed while having a most delicious dinner. We shared a variety of tapas, one of which was a very tasty rabbit dish. At one point I almost chocked on my food when WB started a sentence with “When I was talking to Corey Gardner last week”. (Cory Gardner is a Republican senator who is up for re-election in November). WB talks with most of the local politicians on a regular basis for professional reason. Our conversation briefly detoured to politics. WB had no kind words for our gay Governor, Jared Polis. I steered the conversation to other topics. Overall it was a most enjoyable time. WB is easy to talk with and always seem to be up for an adventure. WB had three drinks with dinner so I drove his Tesla back to his house. I should say the Telsa and I drove back to WB’s house as WB wanted me to experience to self-driving mode. Giving total control to a car was bit scary. The car is another sweet drive and is unbelievably fast. The rest of the evening was spent watching Netflix and cuddling in his media room. WB threw me out around ten as he had been up very early to go hiking. WB may not be Mr. Right but he is entertaining.

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Two Sons?

As if this day was not going to be interesting enough, Bruce, Mr. 28, texted. He misses me. He wants to get together again after he presents his final business plan to the investors. I thought one son was enough. I feel like I got off the roller coaster and got on the scrambler.

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Defining Aggressive

WM, the wealth manager, is taking me to dinner tonight for Daddy’s Day. He also has a gift for me. I question if it’s too soon for gifts. I’m hoping it’s something insignificant. I’ll find out in a few hours.

WM is aggressive. He told me he goes all in. He goes for what he wants. He told me he had to be aggressive to build a company that now employs 50 people. My online profile says I’m looking for fun and adventure. WM brings both to the table. Along with aggression. He is the epitome of aggressive. I feel like I’m sitting in the front seat of a roller coaster inching its way up the first incline. I know the ride is going to be fast and furious with lots of twists and turns. Will I get back in line when the ride is over?

In other news, I had a walking date with the guy I am interested in, but he doesn’t feel the same way. On our walk last night he told that he really enjoys my company. He would like to have more than a friendship but he has ED. He doesn’t want to take any of the ED medications. Any type of sexual relationship would be one sided. I didn’t ask why he was opposed to ED meds because it was a very tender moment. He bared his soul to me. I didn’t want to be intrusive. It’s a conversation we can have at a later time. I had a great time on our walk and our post-walk dinner, which he paid for. He wants to get together again as friends. I’m good with that. He’s a man with a many great qualities. Who wouldn’t want a friend like that? Besides, I have my hands full with WM.

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He Cleaned

The wealth manager texted pictures this morning showing his bedroom had been cleaned with the bed made. The nightstands were decluttered and there was nothing on the floor. He also sent pictures showing the rest of house had been cleaned. I hope he keeps it clean as I don’t have time to see him this weekend.

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I came across an interesting profile online. After some banter back and forth over several days, I realized I had met this man before (read here and here). We had a lunch in 2015 but he dropped me because I didn’t text him for three days. Five years later, he has a new haircut due to less hair and has put on some weight, which he wears well. The weight gain is puzzling as he is an avid runner and cyclist. I’m guessing he has a poor diet.

We had our second date yesterday, five years after the first date. We went to the Denver Botanic Gardens and then had dinner at Kona Grill. I had a great time. Somethings hadn’t changed, others had. He’s still a great conversationalist and a successful wealth manager. He runs with the affluent professional gays and is friends with the beer heir and his husband who live a few streets away from me in a palatial house. He lives in the same Congress Park bungalow which is charming on the outside but still looks like a frat house on the inside. His bedroom was a mess. It looked like the closet exploded into the room. Dirty clothes covered the floor, the bed was unmade and the nightstands were cluttered. It’s not how I expected a 44-year-old to live. He traded up to a Tesla Model S from a Ford Focus. He’s still a Christian and recently got a tattoo on his upper bicep depicting Christ nailed to the cross. And now he wants a Daddy. He’s asked me out for a third date. I summoned my inner Daddy. I told him to clean his bedroom and make sure the bed was made with clean sheets if he expected me to spend any time in there. He simply said, “Yes, Sir”. I said nothing else. I walked out of his house and, got in my car and drove home.

An hour later I received a text thanking me a nice evening.

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Saturday and Sunday

I had two walking dates this weekend. One on Saturday afternoon and the other on Sunday afternoon. The Saturday date went well. We walked for four miles along the South Platte River. After the walk, we had dinner at a restaurant near Confluence Park. It was my first time eating in a restaurant since Covid-19 arrived. My date was two years older than me, and thankfully, HWP like his profile stated. I had a great time on the date. The conversation flowed effortlessly. We are both self-made with similar childhoods including Catholic educations. The Sunday date didn’t go so well. The guy was at least five years older but looked a lot older than his photos. He was out of shape and didn’t want to walk very far. We ended up having a conversation while sitting on a park bench. Why agree to a walking date if you can’t walk very far? While I found him interesting there was no spark. He put no effort into his appearance and probably hasn’t worked out in years. And then there was the nose hair. There was no way I could see myself getting physical with Mr. Saturday.

I was interested in pursuing Mr. Saturday but he has moved me into the friend zone. We have tentative plans for a second walk. Mr. Sunday is interested in seeing me but I moved him into the friend zone, which he didn’t take very well. It’s odd how things worked out.

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My friends have been urging me to join Scruff for a year or two. One even threatened to set up a profile for me with recent pictures from one of our walks. I finally gave in to their pleas. I created a profile. I got my first “woof” in a matter of minutes. The sender was a tall, lean and hairy young man of 30. He was handsome and beautiful. At least he was slightly older than Bruce. A few minutes later he messages me:

I live to serve alpha men. Men who know they are superior. Who don’t give a fuck is I like whatever they’re doing. I have a sick need to be degraded and humiliated and controlled, used and abused. I fantasize about being brainwashed and blackmailed. I need a guy who doesn’t listen to safety words.

I couldn’t help but wonder why he thought I would be what he needed. I thanked him for messaging me but let him I wasn’t into degrading and humiliating men.

The second “woof” came about an hour later. This one was sent by a 28-year-old man who happened to be blind. We chatted back and forth for a while. His messages were well written and nicely composed. I let him know I was looking for guys closer to my age. He still messages me. I still respond. I can’t imagine the challenges of gay blind man must face given how judgmental the LBGTQ community can be at times.

The third message came from a 40-year-old married man. He let me know he likes hot daddies. I clarified he was married to man in an open relationship, and not, cheating on the side. As you can imagine, dating was not his priority as he already has a man. He demanded nudes from me while he only had a face pic. In my book, you better send me a nude before asking for nudes. He finally sent a shirtless picture to me but no nudes. I’ve been ignoring him. I don’t need another married man in my life even if he is in an open relationship.

The final message was from a 65-year-old with no pictures. A picture less profile is a major red flag for me. His profile said he was HWP. We chatted for a while. He let me know his neighborhood and that he owned a single-family home. It was like he was showing off merit badges for home ownership and living in mostly white, but hip, neighborhood. He finally sent a picture. I guess I have a different interpretation of HWP.

Most of the guys looking at my profile are much younger than me. The “woofs” have stopped for now. In the age of instant communications and 24 hour news cycles, I’ve become stale. I’ve had my two days of being a fresh face. One young man told me I didn’t look a day over 49. Little did he know I took 2,000 selfies to get the one I chose for my profile picture. I guess, I’m destined to be cast as a daddy, or in some cases, a grand daddy.

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It Was Fun

I ended it with Mr. 28. He needs to focus on his start-up and really didn’t have a lot of free time. Also, I’ve been with a guy who put his career first so I could see what the future looked like. I didn’t expect it to be a long term relationship. I will always have fond memories of him. It’s probably the last time I will be pursued by a handsome rich man more than half my age. I will always have fond memories of him. He still texts and I’ll be going to the launch party. He’s not completely out of my life.

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Not What I Expected

Friday night did not turn out as I expected. I planned on talking to Bruce over dinner so I could be out of there in two hours. I ended up talking to him for five hours, leaving a little after 11.

Bruce told me he was cooking dinner but that didn’t happen. He got caught up working on the business plan for a new venture. He ran the elevator pitch by me but wouldn’t let me read the plan because I had not signed an NDA. Bruce is serious about business and being successful. He’s raised $2.2m for the new venture. I’m guessing most of that is coming from his family. We ended up picking up take out from a restaurant down the street from his building. I was impressed when he offered to pick up dinner for the concierge. He treated her as an equal and not the help.

We traded questions over dinner trying to get to know each other. I found out Bruce gets his entrepreneurial spirit from his father who has started and sold a succession of businesses. He grew up in a 24,000 sq. ft. house in a small midwestern city. He’s been given every advantage in life one can be given. He fully acknowledges he won the birth lottery. His parents expect him to be philanthropic so he’s looking at how he can give back to his new community.

Bruce’s apartment, in a full-service building, is almost as big as my house. It’s beautifully furnished. The views of downtown are stunning during daylight and even better at night. He’s got great art. At least the pieces that have been hung. Bruce still has to uncrate and hang three large pieces which were delivered on Friday afternoon. The art must be pricey as only art of a certain price point is shipped in museum quality crates.

Bruce is wicked smart. He know what he wants and he goes for it. He’s handsome, physically fit and very charismatic. I’m usually not comfortable on first dates but I felt totally at ease with him. I’ve had countless first dates (many have been documented here as disappointment drives) and it’s been a long time since I had one with a man who I felt an instant connection with. I often found myself trying to find one thing that would make we want to see the guy again. I never expected to feel a connection with Bruce. Given the age difference, I expected an uncomfortable evening with a man I could not relate to.

Bruce has always dated older men. He finds guys around his age are intellectually lacking. He wants to be around men who can hold an intelligent conversation and stimulate his mind. I seem to have the qualities be desires in a man. Bruce’s parents and family are fully aware he dates older men. They accept his choices as they want him to be happy. Thankfully, I’m not older than his father.

I questioned Bruce about his hook ups with the guys in my social circle. I told him I was not comfortable that he’s been with my friends. Bruce said it was just sex. A man has his needs. As I expected, there are guys he plays with and guys he dates. He laid out his rules for dating. No sex on the first or second date. After the second date there has to be a cuddle-only sleep over. No sex until after the sleep over. He’s monogamous when dating. It was not clear when in the dating process the activities with the playmates stops and monogamy begins.

All evening I kept a physical distance between us. We were not wearing masks. As I was getting ready to leave, he moved in for a kiss. I threw caution to the wind. At the time, it felt like the perfect ending to a most enjoyable evening. It felt so good to hold a man in my arms. Had I been touch starved? I can’t remember the last time it felt so good to hold a man at the end of a date. Usually, I’m hoping they don’t want to kiss and I’d cut off my arm to get away from them.

As I was pulling out of the parking garage of his building, I was suddenly slapped with reality. I just blew two months of self-isolation and mask wearing. I guess I’ll find out in two weeks if I’ve been exposed. I don’t regret kissing him but I am disappointed in myself for letting my desire for physical touch endanger my life. I’m not naïve. I don’t think I’m the only guy he’s seeing. I don’t know how many guys outside my social circle he’s hooking up with. Bruce told me he doesn’t know anyone who’s had COVID. He has not been tested. Could Bruce be my Typhoid Mary?

Bruce texted me when I got home to thank me for a wonderful evening and great conversation. He told me I could have spent the night. I told him it was best I didn’t. He’s looking forward to the next date.

There were a few texts on Saturday afternoon. Just generic how is your day type messages. It’s been radio silence since. I’m not sure how to proceed. I’ll respond to his texts but I’m not planning on contacting him. I need time to process what happened. How do I solve a problem like Bruce?

I’m not going to beat myself up over kissing Bruce. I have to accept the consequences of my actions. Is it just to blame my behavior on touch starvation? I’m not sure how to move forward. It’s been a while since I’ve been excited by a man. I allowed myself to be put through the ringer by detective. Am I allowing myself to be played by Bruce? Why did I have to meet him during a pandemic? Why isn’t he being more cautious? Why did Morgan invite him on that hike? What am I going to do?

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The Friend Column

One of Morgan’s online friends has taken an interest in me. Morgan gave him my contact info after a group of friends, all 60 plus, had a socially distant hike. Morgan invited the guy on the hike because he likes older men. The guy shows up in a new Range Rover Sport. A nice car a guy who is only 28.

He started texting me that night. The conversation was social so I didn’t think much about it. I find out he lives in three-bedroom apartment in LoDo. His parents are “helping” with the rent while he reboots his real estate career. A google search tells me the rent on a three-bedroom in his building starts at $8,000 a month.

Last Sunday, he was invited to Morgan’s 71st socially distant birthday party. We had polite conversation which he also had with most of the guests. The guy can work a room.

He started texting on Sunday night. He wanted to know if I knew a local lawyer specializing in LLCs and S-Corps. The conversation was friendly and centered on the city and what it had to offer.

He texted on Monday asking how my day was going. We exchanged pleasantries and that was it.

Tuesday morning I get a good morning handsome text along with a picture of him shirtless in bed. He asks me if I like to cuddle. He tells me wants to have movie night with me, cuddling under a blanket with my arms around him. I tell him I thought I was in the friend column. He tells me everyone starts out as a friend. Plans are made to get together on Friday night.

Being 63 makes me hesitant about meeting him on Friday night. I talked with the architect who has also met the guy. The guy has been texting the architect too, but it’s more sexting, than texting. The architect tells me the guy has hooked up CJ, another friend. The guy wants to have a three way with the architect and CJ. Three ways must be his thing. The architect has not been asked to cuddle on a movie night. I guess there are guys he cuddles with, and there are guys he simply plays with.

I can’t say I’m not flattered by the attention from a young man. Physically, he ticks off all my boxes. He’s educated along with being a great conversationalist. What I’m not thrilled about is the age difference. There’s a good chance I’m older than his father. What bothers even more is he’s hooked up with Morgan and his husband, CJ and wants to hook up with the architect. I don’t want to be involved with a guy who’s having sex with my friends. I also wonder how many other guys he’s been with in the six weeks he’s lived here. And I wonder about COVID exposure.

I still plan on meeting him tomorrow. I will not be cuddling under a blanket watching a rom-com is his pricey apartment. I’ll be socially distant while I explain why I need to keep him in the friend column. It’s a conversation I want to have in person so I can control the narrative.

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