Dating on Empty!

You don’t have to be rich to find happiness!

She took the house, the only decent vehicle you had in the garage, and some part of your dignity for a while.  Welcome to the club, freshly single man, you are now officially divorced.  We don’t hold any “secret” initiation rituals.  Why?  Because we can’t afford to!  Divorce is expensive and more than likely 70% of your salary has gone to pay for an attorney, who gladly watches and holds your hand as they lead you to poverty with a smile.  Another 20% is going towards the essentials like rent, electricity, and Netflix.

What does that leave you?  A whopping 10% to go have a whale of a time living on peanut butter crackers and crashing the weekly rodent poker tournament for beer nuts and chips.  Third world country denizens won’t be envious of your diet at times.  As much as you can’t fathom the thought of going out with another woman, eventually you will realize that is an exercise in futility, and it’s time to hit the dating scene again.  Take notes, fellow club member, you have to get real creative at times juggling between reading books by candlelight or showing a potential lady friend a good night out.

There are many books and articles written on re-entering the dating scene.  Read them if you must, but since your aforementioned lawyer has tested the “squeeze blood from a turnip” corollary, you can throw a lot of that advice out the window.  It’s not 1975 anymore, and unless you are Adonis or have the confidence of Leonardo DiCaprio, meeting potential suitors at the grocery store or gas station is rarer and rarer these days.  Hitting the club sounds good in theory, but paying $15.00 dollars for a round of drinks is going to suck your dating pool money dry quickly.  Time to get that online dating subscription for a world that you never in a million years thought you would journey into.

Online dating isn’t exactly cheap either, but, take my advice, and pony up the dollars for a paid subscription when you can eventually afford it.  You are actually taken serious, and you don’t have to deal with a single mom in her 30s from Kalamazoo, Michigan by the username of DoubleDDiana trying to sodomize your computer with her “How to boil water” webcam service.  It’s a new thing for you, and you can go at your own pace until you finally get the confidence to actually ask someone out.

My first date after my divorce was a combination of excitement, nerves, and thoughts like “how in the hell can I afford this and still text her the next day when (not if) they shut off my cell phone service?”  I’m old school and believe chivalry isn’t dead, so in my world, as long as we aren’t eating truffle oil infused brownies for dessert and putting away bottles of Hennessey like water, I’m paying and it’s not even up for debate.  Sushi dinners and a few drinks will get expensive and are not something you will be able to afford all the time.

Luckily, I knew how to operate a stovetop for more than making scrambled eggs, and you, new club member, should figure it out quickly yourself!  I would always suggest a first date be somewhere in public, so there is no getting around a hit in the wallet initially.  Depending if there is some chemistry after that first encounter, you can have a much cheaper second or third date with the “retro” idea of dinner and a movie at home.  Pick up all the dirty clothes and stuff them under the bed, get the weeks’ worth of dishes out of the sink, and tidy up your place.  Make a nice dinner, go for a walk at a nearby park, and then watch a movie.  It’s much cheaper than a night out, and there is a good chance your date hasn’t had someone cook them a meal in eons.

If you are newly single and found someone that has been single for a longer period of time and insists on fancy dinners all the time…. run!  That is a professional dater, and you are nowhere near ready for that, nor can you afford it!  Hook them on the first date by being yourself, and then let your character do the rest.  Research free and low budget activities in your part of the world.  I can’t stress enough, you learn more about a person walking in a park or treating a department store as an air conditioned exercise track in the sweltering summer heat than you would listening to loud music and sweating how much you have in your checking account when the bill comes at a restaurant!

You’re part of a club you never chose to be in, mentally you will eventually embrace it and then wear it like a boss.  Dating doesn’t have to be that expensive if you don’t want it to be.  Bone up your kitchen skills, learn that popcorn and an HD TV is much cheaper at home than going to a movie theater, and, since your single anyway, there should be no reason you are living on the pizza diet and testing the theory of gravity at home!

Send Skipah Sailing!


  1. That would be tip #1 for any guy or girl!

  2. I feel,like I’ve already said this today - but thank goodness I don’t have to do that any more. You’re right though - pay for the service or scrape the bottom of the barrel.

  3. I hope it helps some poor schmuck that finds themselves in my shoes one day

  4. Hi Gary,

    Great advice for everyone who wants to go back to the dating scene. It is true that none will take you seriously on a dating site unless you pay. At least it’s good to know that chivalry is not dead!


  5. I only had one horror story (and it was a doozie) but glad I stayed the course..pun..and found Miss Madison.

  6. Thanks! The whole process sucks if you didn’t choose it. It takes awhile but eventually life does get fun again.

  7. Well you certainly are the expert in the field of finding the perfect mate post divorce as you have landed Miss Madison! I met The Captain on line on a site designated for people with shared fitness interests (ours being sailing). It cut out a lot of the crap. Of course, I have my own on line dating horror stories, but once I got the hang of it, I did just fine.

  8. I know a few divorced guys I’m going to turn on to your blog, Gary. I think they’d find it very helpful.

  9. I passed the dog test on the first try, I’m like some kind of dog magnet. Dogs dig me, just call me the Dog Whisperer, did I say dog enough to get PETA off my ass?

  10. I’ve been in those shoes and you are so right about getting to know someone better and more deeply when you are doing simple things where the focus is more on conversation and each other, not fancy distractions-my now-husband would walk my dog at the dog with me and we talked a lot. Plus, my dog was going to have the final say in whether any dating relationship progressed, so I needed to see how they got along!

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  12. That “we” thing takes a good year to get past LOL.

  13. Haha sooo I was definitely a “professional dater” but not in the sense that I used men for free dinners, just that I went out on dates a lot. A LOT a lot. I once went out with a guy who had just divorced and he couldn’t stop talking in plural - “Target? We love Target!” - there wasn’t a second date.

    On a different note, free online dating isn’t terrible! POF, yes probably, but I met my husband on OkCupid 😀

  14. It’s the best way to stand out of the crowd :).

  15. Haha: “pick up the dirty clothes and shove them under the bed.” 🙂 You’re right though - dating doesn’t have to be expensive and to be honest I was always impressed when a guy would come up with a creative/more thoughtful date than the old standard dinner and movie bit.

  16. I can imagine, Gary. Still, it has to be better than serial killers dating you. 🙂

  17. It was a interesting journey to say the least, but hey I found Miss Madison out of it so it was worth it!

  18. Yes, I completely agree - dating doesn’t need to be as expensive as people make it, and it is often more fun and comfortable to do the cheaper, simpler activities anyway. The people worth being around would never expect someone to stretch their finances beyond what they can afford just for the status of fancy dates.

    I think you’re right about the first date though - must be public. Especially when online dating. If you started insisting a first date must be at your house, with you cooking too, you are inadvertently saying, ‘Please let me eat you.’

  19. those dating websites look like the scariest thing in the world to me but they are the best resource for singles and I guess you just have to figure out your way through them without being eaten alive - think I’ll stay married for now 🙂

  20. The serial daters kill me!

  21. It had never occurred to me until you mentioned it, Gary, but that part about the serial daters made me smile. The advice that followed it also made a lot of sense to me too. I mean, it’s better to be natural right from the get go, which means getting away from fancy restaurants for a while. If the only time two people ever get on well is when one of them is blowing through a ton of money, then maybe it was not meant to be.

  22. I don’t think my species will ever figure out how much of a bonus it is if you know how to operate a stove top. 🙂

  23. I hope you at least replaced the fried chicken!

  24. Thanks Rica! High five back at ya :).

  25. Yes. A man who cooks will turn my head, add in a sense of humor and my knees start to buckle. I met my chef through e-Harmony and believe me he was worth every penny! And here’s another dating tip: Don’t forget about hiking. Great way to meet someone who is a self-starter and minimalist.

  26. I love this! You made me laugh. What an encouraging post! I married for love, I mean seriously, the guy actually stole the flowers out of a vase at the restaurant we were at once. One time he went to his mothers house and cleaned out all her fried chicken so we could have a picnic. Did I mention he made me laugh? He did and that was better than all the wining and dining in the world.

  27. I agree with the online dating. True, you hear your share of horror stories but I have had success with it. After a decade-long marriage to my chronically cheating ex, I was not down with the dating scene. It took me 5 years to get in the game, and online dating helped me ease into it without ever leaving my home. I enjoyed this post, and your sense of humor. Thanks for sharing! Here’s a virtual high five and thumbs up for your chivalry. I am not too proud to let a man pay! 🙂

  28. Your story and Miss Madison’s are eerily similar LOL. Congratulations on continued happiness!

  29. I have been the freshly-divorced female and it was not fun. I met Mr. Halfa1000miles on Yes, I sure did. I didn’t tell anyone or let him tell anyone for years, but after 12 years, we’re quite the success story. I knew pretty soon I was going to be his friend. The dating ages he was looking for was age-appropriate. That was a big plus. Don’t be 40 looking for 20… And not once did he try to pretend to be anything than what he was. We were best friends for 6 months. He won me over with his niceness. Now we are the happiest married couple I know. Online dating is not for losers. He was only the second person I met on there and the first I met in person 🙂

    I was a cheap date cause 1. I’m not fancy, and 2. He cooks.

  30. First couple of days I thought I was some kind of super stud with these beautiful woman hitting me up LOL, then I found out real fast I’m no George Clooney!

  31. LOL. Wow! I get it. Yes, that counts and you need to be a regular on The Huffington Post too. Let’s make that happen!

  32. You captured my experience with dating after divorce just about the way it unfolded. Your advice to invest in a paid dating site is very good. Many are a bit sketchy and could lead to complications. I ended up using eHarmony which has worked as advertised.

  33. Thanks for all the adulation Double T :). I made yahoo finance pages does that count? It was my experience when I was a young naive dumbass in online dating world, that if you had a free profile the amount of sexbots that would message you was staggering!

  34. Gary once again this was awesome. You should really write for The Huffington Post. You have a point of view that the world needs to know about. This part killed me though: don’t have to deal with a single mom in her 30s from Kalamazoo, Michigan by the username of DoubleDDiana trying to sodomize your computer with her “How to boil water” webcam service. I was dying. Really? You’ve encountered these women?

    I would also like to note that some women are not professional daters. I don’t go to a man’s house until we’ve known each other for a while. People are crazy. However, I will offer to pay for some dates so he doesn’t always have to forego his cell phone bill to take me out. I like walks in the park too with a hot dog and a bottled water. Women can be flexible.

  35. You have to swim in an ocean of sharks but eventually you find that one girl on a deserted island who is happy they found you :).

  36. Being married with kids ain’t cheap, but being divorced with kids is a certain kick in the butt. Good for you for being real about it! Poser’s are the worst. Can’t imagine what those dating sites must be like. Keep it real and the true real ones will show up. Looks like you found her.

  37. I haven’t seen it but I know I’m getting ready to :).

  38. Great advice and so true from us club members. I’ve decided to get back into dating this last week. Not going to well though! But twitter is on my side. Have you seen @pickinguptoys (as well as, sadly, many others) campaign to get me dating?

    Oh well, one day.

  39. For a guy that hadn’t been single since he was 20 years old it was a whole new world for me. Actually got fun for awhile, but it got old pretty fast also.

  40. That’s the girl I met :).

  41. I wouldn’t wish it on anybody pal!

  42. Great advice! I could never do the on line dating thing. I have trust issues. Really this is great advice for any divorced man/woman. Sometimes we are the ones who had to pay through the nose. I’ve been on one date in 2 years. The next day he sent me a text telling me he was in love. I told him, No you are just lonely. I’m much better with fictional (book) boyfriends!

  43. I love love love this post. From beginning to end it was so honest and charming. My favorite line, “who gladly watches and holds your hand as they lead you to poverty with a smile”. Not my favorite cuz it happened, but just because of the diction. I’m sorry that so much has been taken away from you since your divorce, but I truly hope you find someone amazing who won’t mind walking into department stores just for the AC.

  44. Thank you, Gary, for once again making me glad I don’t have to worry about this. Or at least I hope not! Asking wife now….”Hey dear, we’re good, right?

  45. For sure an added bonus!

  46. On-line dating is how I met my husband back in 1993! We married Dec. of 1995 and have been together ever since! Granted had to go out with a few loosers this way first, but eventually struck gold!

    Insisted we go dutch (each help pay) every time, because I was stubborn. Took him a while to figure out the advantage to this situation on his personal budget (he’s male, what more do I need to say?).

    Hold on to the lady you met, she sounds like a decent catch! She gets along with your daughter too. An added bonus to the mix,

  47. Lmao! Dating after divorce especially in this era is a shock! Good tips here! We got lucky with online dating but there are still some funny stories out there! And a true gentleman stands out!

    I laughed out loud at your DDDiana from Kalamazoo! Lmfao!!!

  48. It’s not a fun place to be initially, trust me!

  49. Great tips for sure. I hope I never need them! 😃

Tell Skipah all about it!