Jill Ferguson joins me today to discuss online dating challenges in Las Vegas. She was married for 23 years, and has been divorced for 12 years now. Jill has three adult children and one grandson. Her identical twin daughters are part of Bachelor nation – you may remember them from season 20 of The Bachelor and a few seasons of Bachelor in Paradise, in addition to their own show. Consider Jill your dating-savvy friend who is also trying to navigate online dating in the modern world of dating in Las Vegas.

This episode, we talk about:

[2:23] How Jill and I met (through my mother!)

Jill and I connected through my mother, and she and my mother met about 15 years ago sitting side by side getting pedicures. They struck up a conversation about dating, and they found out that they had both dated the same guy. My mother had been in a relationship with him, but they had been broken up for many years when Jill went on a few dates with him. Jill and my mother hit it off and were fast friends, and I’m thrilled she was willing to share her dating stories and tips with us today.

[4:08] Dating with intention

Jill has been actively dating since her divorce 12 years ago, and she is a beautiful and intelligent woman. She has blonde hair, blue eyes, and she likes to take care of herself and put herself together. She really has a presence about her. She also wants to get married, so she takes the dating process seriously. 

Jill talks about dating with intention. She is not out looking for a good time or a one night stand. She is really seeking that special someone. Jill thinks that we are in very different times now with the online dating opportunities. Back when our parents met, people met “in the wild”. They met authentically, exchanged phone numbers, and went on dates. Now with online dating an social media, men and women are talking to probably 5-10 people at a time. There doesn’t seem to be the same focus, care, or effort put into establishing one meaningful connection when you can be spoiled for choice. You have hundreds and thousands of options with online dating and all the different online forums. In Jill’s experience, a big problem with modern dating is that people just don’t take dating very seriously.

[6:46] Lazy online dating versus putting in the effort

I thought Jill made valid points about our modern dating world. It is so online-focused, and COVID really solidified that. I don’t want to put all the blame on men, but I do think they make up for a large portion of the lack of care. They don’t seem to try as hard, and they seem to become lazy. It can be frustrating for women who are focused on finding a long-term partner or a spouse.

Jill shares the words of Esther Perel, who is a relationship coach and therapist. She starts a lot of her online messages by saying that if people would put as much effort into their relationships as they put into their jobs, we would probably have a much different outcome. Jill thinks people often don’t understand how disjointed that focus is. A job is a job, but love is really the most important thing in life. People think they have time, but time is a thief. 

Let’s say a man gets divorced at 40, and he dates and plays around for 5-10 years. Now he’s 50 and he still hasn’t found someone. Now he’s 55 and he still hasn’t found someone, and he’s wondering why. Maybe it’s because he hasn’t put in the effort, but instead has just kind of been playing around. We don’t know how much time we have left here, and as we get older, our bodies start acting differently too. Jill points out that men think they have all these options, until they face their fifties and their parts stop working. People just get very selfish, and they think they have all the time in the world. Really, the years just fly by.

[10:12] Making a good impression while dating

I asked Jill to share about some of her recent dating experiences to help us understand some challenges of the modern online dating world. She has tried to keep herself open to dating where she lives in Las Vegas, NV, in addition to nearby areas in California, Utah, Arizona, or Colorado – something that is maybe a two-hour flight or less, in the same time zone. You have to be practical about certain things. 

She met a very nice gentleman online, and he flew out to Las Vegas to meet her. They went on two really great dates to incredible venues, so she could tell he really researched it. He set everything up and made all the reservations. That was perfect.

Jill also shared some of the challenges, and although she tries not to be overly critical of these things they do matter. One of the blaring things was how he was showing up dressed for the dates. He was not dressed to impress, and Jill really dressed to impress. She goes all out for dates from hair, to nails, to lashes, to tanning, to a nice wardrobe and nice accessories. She has always been a very “put together” person, but she really goes the extra mile for a date. 

At first, she decided to let the appearance slide a bit on the clothing. Some men aren’t the sharpest tools in the shed when it comes to knowing how to dress. So they had two great dates in Las Vegas, and then he invited Jill to see him in his home. That day, she got up early in the morning and dressed up as if she was going on a date. That’s not always the easiest or the greatest when you’re going to be traipsing through an airport in heels, but she wanted to step off the plane looking amazing. She wanted to make an impression. 

When her date picked her up, he was dressed like they were going to Costco. It took the wind out of her sails, and she was super disappointed. It was so bad, Jill was borderline embarrassed to be walking through the airport with him. She told herself to suck it up, and they went to get her bags and walked out to the car. He drove a very nice, expensive car – but when they got inside it Jill saw that it was filthy. The carpets were dirt and there were cans in the cup holders. She thought to herself that this was probably a good indicator of what the house was going to look like, and it was. The house was not updated and not well put together. He was an antique collector, but the house almost looked like he was a hoarder. His children were fully grown and out of the house but still had their books on the bookshelves. There was an elliptical next to the couch in the living room, and his desk from when he was young was nearby. The washboard his great-grandmother did their laundry on was on a shelf in his living room. The master bedroom featured crushed red velvet drapes, and looked more like a whorehouse than a home. Jill smiled and got through, and he was a really nice person, but everything put together was a complete chemistry killer.

Jill wishes that men understood the importance of a first impression. When you allow a partner into your home, you are showing that person a lot about yourself. How you live tells a lot about you, and you won’t get any further in a relationship if you don’t have that chemistry and connection.

Even if you haven’t dated in a long time, or your ex decorated the home you live in, you cannot stay stuck in the past. We need to modernize ourselves to get ourselves ready for the modern dating world. We need to update our profiles, update our houses, and make sure that our cars are clean. Jill thinks these things matter to a lot of women. She has a lot of single friends, and they all run into the same scenarios. It’s like men kind of get stuck in the Twilight Zone, and women try to be a little more progressive. We want to be fresh and current and make that good impression. 

[21:05] Jill’s top three dating challenges

Jill shares her top dating challenges are effective communication, chemistry and connection – and she also adds lifestyle to that list.

[21:57] Dating in Las Vegas: Lifestyle challenges

I asked Jill if she thought dating in Las Vegas had any particular challenges due to it being the entertainment capital of the world. She has single friends all over the United States, and it seems like they face similar challenges regardless of location. 

When it comes to lifestyle, Jill does acknowledge that there are so many things at the fingertips in Las Vegas. There is easy access to drinking and gambling, and she has met plenty of men with big gambling problems. They will go on a date to a casino, and before they go to dinner the guy will have to stop and cash in on one of his tickets at the sports book. Then Jill starts thinking that’s how he is going to pay for dinner tonight, and it’s a bad look. Drinking is another thing that’s not for Jill, and recreational marijuana use has also become huge because it is legal in so many places. People are really into smoking pot and taking edibles, and none of that fits into Jill’s lifestyle.

Jill is a light social drinker, and she thinks it’s great to have fun. It’s great to have a few drinks, even get a little buzz – but when it goes past that, at this age and stage of life, that is a problem for her. Again, she doesn’t think that is unique to Las Vegas. Drinking can be a problem anywhere. 

She would like, however, to meet somebody who could make her life a little bit better. She lives in a house, and she would very much like to meet someone who is also living in their own home. No roommate situations, no apartments, and no staying with a friend while they figure out what they want to do or get settled after just moving here. Sometimes Jill feels bad for feeling that way, but that is truly what matters to her. She would like to know that someone is stable, has roots in the ground, is strong, and has made something of their life. He should have a stable career, and not be jumping from one career to another. 

At this stage, many people in the dating pool have been divorced – some people more than once. They should be getting to a point where life should be getting easier, not more difficult. Chapter one is done, and now it is time to move on to the second and final chapter.

[27:26] Men’s false security when dating

Jill says that she doesn’t think that men necessarily do this on purpose. Somehow, many of them don’t know better. She has always felt that men look at themselves in a better light than women do. Women always feel like they need to lose 10 pounds, get Botox, or get plastic surgery. Men seem to have this kind of false security like they are better looking than they really are, or that they are much better than most men out there. They think they look great when they show up to a date in jeans and a t-shirt that has been in their closet for 15 years.

[30:00] Dishonesty in online dating profiles

Guys will post pictures of themselves from 10 years ago in their online dating profiles, where they’re 25 pounds lighter. They will add 2 inches to their height. Jill now asks men when they start talking if all of the information in their profile is accurate and current because she has found most men lie about their age and height. They will lie about their age by as much as 10 years, and Jill thinks that is a horrible way to start a relationship. She has an age range set in her profile that she is trying to match with because that is the age range that she wants to date. Men will say they are 55 because they want to match with women that are 40, even though they are really 60. There is a lot of dishonesty and false reporting out there, and it’s not fair. People deserve to have accurate information upfront.

[32:41] The impact of Jill’s daughters’ fame on her dating life

I asked Jill about the impact of her daughters’ fame in Bachelor Nation on her dating life. She hasn’t found it to be an issue, and she tries not to talk too much about her children when she is just getting to know somebody. One someone gets to know her and she opens up more, sometimes they will comment that they are dating someone famous. Jill is adamant that she is not famous; her children are. They are a part of her, but their lives are separate from hers. She has never really had it become a problem, but it is fascinating to most people when they do find out. They are usually very curious and will ask a lot of questions.

[36:05] Including family members in an online dating profile

Jill asked me about including pictures of family members in an online dating profile. She has never included pictures of her children or grandchild. I don’t think it should be done, and Jill agreed. She has seen men putting pictures of their minor children on their profiles, and it’s cringy. It’s inappropriate and exploitative.

[38:33] What Jill hopes Celeste Moore Image can do for men

Jill hopes I can support men to understand the importance of knowing how to show up for a date. They should know what to wear, appropriate topics to discuss, and how to have reciprocal conversation. Appropriate communication and showing up looking fantastic would be great. They should have a good haircut, they should be well groomed, and they should have great teeth and a nice smile.

[40:33] Where Jill would be if she could choose anywhere in the world

Jill is very rooted in Las Vegas. She is a native, her children are there, her family is there, and her mother is there. She always feels most at home in Las Vegas. If she could be anywhere, it would be in a beautiful, growing, loving, stable relationship.

Connect with Jill:


Thanks for tuning in to today’s episode! Come and hang out with me on Instagram @celestemooreimage and let me know your thoughts on today’s episode, because I always love hearing from you all!


Online Dating After Divorce with Jill Ferguson

April 11, 2022