Dating in Chicago: Younger men
So I’ve been toying with the idea of writing this forever (or maybe two years). What’s dating like in Chicago (or everywhere, I’m still learning)? The 2019 (my) version of Sex & the City and what actually happens now in dating. I LOVE watching old episodes of Sex & the City and relate to all the characters and the situations that occurred. What would that show be like now? With online dating, the availability of texting, chatting, cell phones, swiping, lack of follow through, filters, social media, would the girls have the number of relationships they had on the show? Many of Carrie’s suitors went onto many dates and into semi relationships. Nowadays, we are lucky if anyone gets a dinner date or even if they show up lol! So. . . I’m attempting to start a series (but I’m not promising how many blog posts a month) called Sex and the Chi-City where I share my thoughts about dating and funny stories. Don’t worry, I won’t be too graphic as I know family and friends read this and it has been hard enough to date in general when they find out I blog! This may make it even harder, but I love sharing and the amount of funny stories I’ve shared with friends is maybe a great read for you. Sign up for my blog post updates here.
I want to hear from you ladies! I’ll change it up with interviews and stories you have and hopefully, this is a fun read for all you ladies.
Sweater and leggings $100 and under
Whether or not you are dating, married, single, etc I hope to bring laughter and insight as to what it is like dating now after being with someone for 12+ years.
Let’s move onto younger men. You see those screenshots above. They are from a popular dating app that allows filters, likes, and messages from both sides. I’ve probably been on it for less than a few months and have collected a ton of funny messages, but the one that sticks out to me is the number of 19-26-year-old men that message me to be their sugar mama or basically have a “fun” time. I asked around when I started getting these messages and there’s a rumor out there that divorced women are the best to “date” as they are looking for fun and don’t care. Where have I been? LOL. There are older women out there looking to be a cougar and love the younger men. I say, “you go girl” if that is what you want to do, but personally, I want a lot more. I don’t have the energy to take care of someone else or teach them what to do. I don’t want to look at someone and feel like they are my child, and I CERTAINLY do not want to support another BOY and be a sugar mama. This mama would rather buy a pair of Louboutins or a Chanel bag then spend it on taking you to Taco Bell. I’m hugely complimented that they think I’m attractive, but who knows how many women they are sending this message too. Also a sign of the times, you could message 100’s of women and get 10 back. It’s a numbers games people and sometimes some prefer quantity rather than quality.
One thing really bothering me about these messages I received is that I’m raising boys myself and I pray that they don’t ever send that type of message or photos to an unknown woman. “Obedient”, “fun”, “hung” would these two boys ever want their sister to receive those messages or would they send that out to a close friend? What happens after you go on a date or meet up is a different story, but the lack of character at all in these first messages shows how hard it is to date these days. Ten years ago, none of us dared to send weird messages like this. I mean emails, phone calls would be inappropriate to start like this so why is it ok now? I want to teach my boys that if you wouldn’t say it over the phone don’t text or write it at all. I’m no prude, I’m not saying you can’t text things once you’ve established that, but most women desire a deeper connection than these messages convey. There are a million ways to word things to sell yourself to someone online to meet, but this girl isn’t sold on young cubs looking for support. I do not judge those that want to do this and I honestly want to know if these notes work on women? If they do, PLEASE email me – I’d love to hear more!
I’m ok with dating younger as in like 5 years. Maturity of each individual is different so I like to see based on the person, and I do prefer someone who knows what they are doing in their career. As I’ve said before I’m not looking for a relationship but I certainly have some guidelines of what I’m looking for, in case, I wanted anything more.
Samantha (from Sex & the City) would have a ball dating these days. Younger men are even more available 24/7. Charlotte, however, would struggle as the romanticism of dating is harder to find. Is it too hard to ask for some old fashioned phone calls and effort?
Could I date someone in their 20’s? I’m not sure? I spent much of my 20’s figuring out my career, myself, and what I wanted. And believe me, I’m still figuring that out! Life in my 20’s is so different than my life now with my kids and just a more solid head on my shoulders. I’m just not prepared to help someone figure out their life and most likely they want kids. What really intrigues me about these notes is if it works and if people (women) meet in person to have “fun”. I don’t fault these men, I just think they could be smarter about the approach if that’s what they wanted but women/young ladies do this as well. Looking for a richer, stable man to take care of them. I mean there’s a whole app that is dedicated to this (Seeking Arrangement). I learned about this recently and was blown away. Oh wait, I just searched online for it and it’s for Sugar babies and Daddies and Mommas! I’m laughing.
What it comes down to is what am I looking for? I’m still figuring it out. But man, dating is hard now. I’m definitely not a Sugar Mama or looking for a Sugar Daddy, but if someone is, send them my way because I’d love to interview them for this series! What happened to bumping into someone in person and falling in love on the first date? My romantic heart has settled on hoping this still can happen :).
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