
| send emails with dating questions to debbie@redcarpetconciergeofchicago.com |
| Dear Debbie Sue, I enjoyed reading your two books. I can relate to some of the dating stories you wrote about. I would appreciate any advice you can give me. I'm in my late 30's and dating a man in his late 50's. He has a 23 yr old son. I met him through an online dating service. I am divorced with no children. We went out to dinner on the first date and talked for several hours. Our second date we went to dinner and a movie. I enjoy his company. He calls me everyday to say hello. He now asked me to go away with him next month to visit his son who lives out of state. He invited me for a weekend trip. Should I go? Is it too soon to go away with him? I hardly know him. I appreciate any advice. All the best, Cindy Dear Cindy, Thanks for writing. It appears this man is rushing things a bit. I totally understand why you're hesitant to go away with him at this time. You've only gone on a couple of dates and now he's asking you to go away with him? It is too soon. You said, you "hardly know him," and you don't. You sound like you enjoy his company and you would like to get to know him. That is exactly what you should tell him. That you enjoy his company and would like to get to know him, here, and not in another state. If he is interested, he'll respect your decision and he'll understand. Good luck to you, Debbie Sue |
| ...from "Still Dating" Pick a Winner I didn’t give up very quickly. I still tried to find someone special in the grocery store. On this day, I saw someone waiting for his number to be called at the “fish” counter. I started to talk to him. He was wiping his nose with his hand. I thought he may have had a cold, but he didn’t sound like he did. He told me he was a vegetarian. He was very skinny. I joked around with him and told him that I was a good cook and could help him, “put some meat on his bones.” Then he started to put his index finger into one nostril, and then started picking at his nose. I never saw anyone do that while I was talking to them. He ordered his fish and told me that he had a nice time talking to me and asked me if I was single. Of course, I replied “yes” and he asked me out to dinner. I told him that we could meet somewhere. I asked him if he had a cold. He said he didn’t and looked at me with a strange look, like he didn’t know why I would ask that question. I thought he had a nervous habit and he would stop after we went out together. We both decided to meet the following evening in a restaurant in an area shopping mall. We met there and he immediately started picking his nose again. The restaurant was a cafeteria style, it had a place to order and you seat yourself. We both ordered a sandwich and sat at a corner table. We talked for a minute before the food arrived. My date kept picking his nose with different fingers. I was losing my appetite from watching him. He was very friendly and attractive but he wouldn’t stop touching his nose. Finally, the food arrived and he stopped for a few minutes. After we got through eating our sandwiches, he continued to pick his nose. He asked me if I would like to have some dessert. He asked me to follow him up to the counter and look at the desserts. He said, “Get anything you like.” I said, “No, that’s okay, you PICK.” Impeccably Clean I dated this sweet man who liked the health club for almost two months. I liked the way he dressed. He was fun to be with. We went out for a few weeks before he invited me to his home. He lived in a nice condo not too far from my home. We picked up some dinner and rented a movie. I liked his condo. It was very neat. He said he was a “neat freak.” I never saw another man’s home that was that clean. It looked like he had a maid everyday. I found out why it was so clean. He invited me to spend the following weekend at his condo. He knew I liked to cook. He wanted a home cooked meal made by me for a change. I asked, “What do you mean?” He said, “During the week I sponge dinners off of my mom. I go to her place. I don’t know how to cook.” He had some leftovers and condiments in his refrigerator. He said, “My mom hasn’t gone grocery shopping yet. She was busy this week.” Confused I asked, “Your mom? Don’t you buy your own groceries?” He said, “No, never. My mom buys them for me.” I was very surprised at what he said. The following weekend I went grocery shopping and was ready to cook him a wonderful dinner. I had an armful of groceries. I got to the door of his condo and heard a noise inside. Suddenly, his mom walked out the door! She said, “Hello, come on in, I was just leaving. I cleaned everything. I filled the refrigerator, washed the dishes and washed the laundry.” I said, “You did all that?” She nodded and then she left. I walked in and saw how clean everything was. I couldn’t believe I was dating a man who had his mom clean his condo. She washed his dishes, bought his groceries and vacuumed all the rooms. I couldn’t believe what I saw next. All his laundry was washed and folded and laying on his bed! His mom washed his underwear! I had to leave. I was about to put all the groceries I bought in his refrigerator before I left, when the door opened. He walked in and said, “Hi, I’m home. What are we having for dinner?” I said, “I got here a few minutes early and ran into your mom. She shopped for you, cleaned everything and washed your laundry.” He said, “Good! I’m glad it’s done.” I asked, “You let her wash your LAUNDRY?” He said with a surprised tone, “Well, YOU weren’t here, so who else was going to do it?” I had only ONE response to that question. I opened his front door, walked out and said, “Goodbye …” Too Many Holes! The following night I stayed at his apartment and I had a fun idea. I decided to wear some pretty lingerie that I brought with me. After he got ready for bed, I got ready. I came out of the bathroom in a pretty silk negligee. He was excited! He said, “Wow, look at that!” I said, “I thought you might like this outfit.” I lay down next to him and he looked closely at what I was wearing. He said, “I think you have to take this back, it’s defective!” I said, “Why?” He said, “It has HOLES all over it and you can see right through it.” NO Touchy NO Feely On our third date I fell in love with the sweet, shy man. Little did I know he was not “into” showing affection of any kind. I was hoping he would change. He told me he never made love to a woman before. We spent a few weeks dating. ALL we did was go to dinner and to movies. He was not a romantic guy. He finally invited me to spend a weekend with him. I was very happy to have some “alone” time with him. The first night I stayed at his apartment, his sister called very early in the morning the next day. It was eight o’ clock in the morning on Sunday. He answered the phone and said, “No, it’s not too early at all. NO, you’re not interrupting anything at all.” I thought to myself, what could she possibly be interrupting? We spent the day taking a long car ride and going to lunch. We rented several movies. We ordered a pizza. We stayed up late watching television. Let’s Play Ball I spent another weekend with him. I had a plan for my shy guy. He liked to watch sporting events on television. His favorite sport was football. He was on a team and he played once a month. I knew where his outfit was in his closet. One night when we got home from dinner, I decided to try something fun. He was in the living room watching a movie. I went into his closet and put on his football gear. I put on his shirt with the shoulder pads, pants with the knee pads and the helmet. Then, I put on a pair of his favorite high heels. I grabbed the football and I walked slowly into the living room. The uniform was so heavy. I couldn’t walk too fast in my high heels. I whispered, “Sweetie, look over here.” He looked up and said, “Hey, that’s a great idea!” I said, “I thought you might like this idea!” He yelled, “Come on, let’s go outside! I’ll teach you how to play!” I followed him outside and thought to myself, that’s not exactly what I had in mind … The Bus Boys I couldn’t believe the behavior of my last date. He was very immature. I was always a big tipper. My philosophy is that when you go into a restaurant and someone is taking good care of you, they deserve a big tip. I am certainly having a hard time finding Mr. Right. I realized that if all else fails I can always count on the bus boys in all my area restaurants. They all love me! They cater to my every need. As soon as I walk in and I’m seated they come running over to the table. They refill my water, I hand them a dollar. They take the plates away, I hand a couple more dollars. They bring me a doggie bag, I hand them some more money. Yes, I’m proud to admit, the bus boys love me for my big TIP’S! Few Words I kept meeting the same kind of men in the bookstores. After work during the dinner hour, I went to another one to hang around the magazines “for men” section. I stood by the “hot rod” and “computer” magazines. There were a lot of men there. I spotted one guy in jeans and a red t-shirt that looked cute. He was tall, but not very thin. I liked the way he looked. He wore nice glasses. I walked up to him. He said, “Hello.” He was a man of few words. I asked him a few questions. He would answer with one word only. He smiled a lot but had very little to say. He motioned to me and pointed to a restaurant next to the bookstore. I asked him if he wanted to go in there and have something to eat. He smiled and nodded his head up and down and said, “Okay.” I was wondering why he wasn’t talking. He just kept smiling. I thought he was nervous and extremely shy. We went into the restaurant. When the waitress came over to the table, I ordered my food. He opened the menu and pointed to what he wanted to order. I still thought he was just quiet and didn’t know what to say. He kept smiling. We ate dinner. I talked to him, and he didn’t say too much. He shook his head up and down. After we ate, he paid the bill. We walked toward the door to leave the restaurant. I asked him another question. I said, “Where would you like to go now?” I finally got an answer from him. He said, “How about a hotel room?” |