On What It’s Like Being Back In The Online Dating Pool At 40

On What It's Like Online Dating At 40

Since I have been single for a few months, I decided to give dating again a try. This might be weird for some of you reading this since you see Jay on here a lot. You might still see him here. We actually were some of the lucky few who had an amicable breakup. But I talked to him about his feelings about me posting this before I decided to because I wanted to make sure he was cool with it. He is, so let me share about my new dating life.

On What It’s Like Being Back In The Online Dating Pool At 40

This is the first time I have dated since my 20s and, I have to admit, it’s been a weird adjustment. I work from home and don’t go out a whole lot to places where I might actually meet someone so I decided to go with 2 dating apps. I made my profiles this past weekend and one has been pretty much a complete bust {I got contacted like 3 times total} so I think I will close my profile there. The other one, though, sheesh. As of the writing of this post, I have received messages from 40 different guys and 144 “Meet Me” requests. You have to upgrade to see who wants to meet you so I doubt I do that. But wow about all the inbox messages.

I used internet dating before I got married and that is how I met Jay and some of the other guys I dated before him. But I remember there being a lot more perverts then {no, Jay was not one of them, lol}. I mean, yes I have run across a few this week but age seems to have mellowed some of these guys out. The percentage of “want to see a nasty pic” {or just sending it without even asking – sideeye} and “want to come to my house” I am getting now is a lot less than I did in my 20s. Thank you, Jesus.

On What It's Like Online Dating At 40

But, I will share with you some of the undesirables I have encountered this week for your entertainment. ๐Ÿ˜‰

Tooth – This guy actually seemed quite promising… at first. Then he got a toothache. And I felt bad for him and tried to be empathetic. At first. Then every conversation after that was about his tooth. Every. Single. One. How he had no insurance. How he was taking expired antibiotics. How he was drinking alcohol trying to kill the pain. How he could finally eat solid food again. Crap. Dude. Go to the dentist already and get that thing fixed. I finally had to just stop responding.

Captain Obvious – Another guy messaged me to ask me if I liked sex. What? I mean come on people. Who uses a dating app who doesn’t? And no. I didn’t respond back because I have a pretty good idea where he was trying to go with that convo. No thanks.

Looking For An Uber – I had a few guys invite me to drive several cities away to see them. Gee could I? No. No offer to meet in the middle or anything. No. Just no. And there was another guy who had no car who wanted me to come pick him up. My name is 4 letters and those 4 letters are not Uber. When I politely refused his promising offer {insert eye roll} he got really insulted saying that I wanted to “use a man for a car.” I have my own car, thank you. Nope, I just want to date a grown man who has his crap together.

A Horse With No Name – There was another guy that I had a date actually set with. Then he wouldn’t give me his last name. I always meet in public first and always with a name {which I promptly Google, Facebook, etc.}. This is the first guy in all of my online dating experience to ever refuse to give me his last name. So, I canceled the date. Then he said something to the effect of it being “your loss.” I just replied, “ok.” After pondering over that for about a half hour, he came back with his last name but I didn’t care for that comment so I never met up with him. First impressions.

Celebrity Interview – And there was this one guy who started a convo with me and then he kept asking me what questions I had for him. It wasn’t like a conversation at all. And he didn’t ask me anything back. So it was me asking a question and him answering. Then him asking me to ask him something else, and so on. I felt like I was conducting an interview for Eat Play Rock, lol. I’m trying to have fun here, not work.

And my personal fave…

Judgy McBiblethumper – Jay and I are separated. We have been for months. We live separately. There is no cheating, lying or any of that. In the eyes of the law and each other, we are good. After telling me all about his sex life with his ex {no, I did not ask to hear about this} and talking about things he wanted to do to me {nope, didn’t ask for that either} Judgy McBibletumper proceeds to let me know how I was going against God trying to have sex outside marriage {again, no offers or requests on my part}. So I asked him how celibacy was working out for him. Turns out he’s not celibate. {insert judgy gasp and eyeroll here} Judgy McBiblethumper might want to recheck his pocket bible since ALL sex outside of marriage is frowned upon by God. ๐Ÿ˜‰

Anyway, I did have three dates this week {one guy I went out with twice and it seemed very promising for a hot second but, alas, no bueno} and I have talked to a few other nice guys. All in all, though, the online dating scene is pretty much a big old SUCK this week, lol. But I am going to take one for the team here and try to let you all know about my dating experiences weekly. I would love to hear about yours in the comment section below. Also, if you have a favorite dating app, let me know. I would love to cast a wider net in hopes of catching something desirable. ๐Ÿ˜‰

About Dawn McAlexander

Dawn is a full time travel and lifestyle blogger. Besides Cheap Is The New Classy, she also owns and writes for EatPlayRock.com, an entertainment site. Her interests include traveling, home decor, DIY projects, organizing her home and enjoying a nice cup of coffee {or two}. She currently resides in North Carolina with her dog, Daisy.


  1. Man I can only imagine that online dating has gotten worse over the years with apps like Tinder with the soul goal of just a hook up. But there do seem to be some good ones that take the time and effort into making real connections. I know that is tough but this post is pretty hilarious. I foresee a series.

  2. I know it must be a hard situation but I’m happy you’re dealing with it with such a positive attitude! Your post made me laugh (and facepalm) so much! The tooth guy was my fav and that other one that kept asking you to ask him questions… LOL seriously?
    ‘their loss’ you will find much better!

  3. Tiara Wilson says:

    I’m not in this situation, but I know that my mom is 40+ and shes been looking to get back into dating It isn’t like it use to be at all. It’s so much harder now because there aren’t as many good guys anymore as there once were. Everyone is either bringing nothing to the table and expecting everything. It’s rough, but I’m happy that you’re going in with such positivity!

  4. I am glad i am not alone with the dating scene being shitty. The ones that piss me off the most are the ones who dive straight into sex talk straight away like mateee wut.

    • Dawn McAlexander says:

      And the sex talk guys, sooooo many of them. I would venture to guess that it was 90% of the guys I talked to in this last month that I participated in online dating.

  5. I loved reading this! I would read online dating blogs all day long haha. I met my husband six years ago and never used an online dating app, but I hear from a lot of my friends that it’s brutal. I feel like it would be entertaining, though, like the examples you shared haha. Ugh! I hope you find some nice, normal people on there! (:

  6. I can’t help but roll my eyes whenever I see the word Tinder…. and there I go and have a flick through all the potential suitors (9/10 being losers!!!!)

    • Dawn McAlexander says:

      Haha! Tinder is one that I have definitely never tried. Oh, the reputation that precedes that site…

  7. I began reading this, stopped, grabbed my dinner and brought it back in front of my laptop because I knew I was going to enjoy reading your blog but was starving too. Yes, life of a single girl who has used online dating sites and who has also written an article about my experiences doing the same thing haha. So I totally loved this!! I have used eharmony and did manage to find a boyfriend who I dated for three years. I wasn’t sure if you were using a free dating app. Maybe you should try one that you pay for; perhaps you may find eww I am going to use the word, better “quality?” hahaha

    • Dawn McAlexander says:

      I have been hearing a lot of good things about eharmony since I started writing about my online dating experiences. I think I might have to try that site at some point in the future to see what all the hype is about.

  8. I was single for 10 years and it was tough, it always seemed there were tons of single women but where were all the single men??? I never explored the online dating world but I do know a few people that have had success with it.

    • Dawn McAlexander says:

      So, did you like the 10 years being single? Like, was it a choice or just circumstance?

  9. I loved reading this.I always wondered if dating site works.
    For sure there are many perverts but one can also get a trustworthy person too

  10. As someone who’s met my fair share or undesirable guys online dating, I know going through this isn’t really all that fun sometimes. I’m so glad that you can but a humorous spin on it, my friend and I are compiling our stories and doing something similar! This was so much fun to read!

  11. Omg, I LOVED this post. I am separated and it’s painful. I haven’t done a date in years. Maybe those typical dudes is why. I am not looking forward to getting back into the dating season.
    Here is the separation page https://viabella-thebeautifullife.blogspot.com/p/separation.html
    I would love for you to share your story here too!

    • Dawn McAlexander says:

      Oh wow. I am so sorry to hear about your separation. I will definitely hop over and check this out very soon. Best of luck if you decide to start dating again.

  12. One of my friends is currently online dating and the stories she shares is an endless source of entertainment for us! I do think that Mr. Judgy McBiblethumper is one of the more hilarious stories I’ve heard! ๐Ÿ˜‰

    • Dawn McAlexander says:

      Yeah, some of these people really shock me. Judgy McBiblethumper was definitely a personal fave of mine, too. Ha!

  13. Oh my this post was entertaining, informative, but heartfelt as well! Enjoyed reading about the profiles of the guys who made the cut and your insight on the modern dating field, too. Haha looking forward to the weeklies!

  14. It’s great that you guys are getting along well — that’s so ADULT of you, seriously! Not to giggle at your expense, but this post was hilarious. It makes me wonder about people, honestly, who share so much inappropriate detail before knowing someone!

    I don’t think online dating was even a thing when I was single, but lots of my friends have met their spouse online. Some of them reconnected with old friends through Facebook and ended up getting married, so that is another avenue to consider.