11 Tips for your First Date after Divorce

first date after divorce

I don’t need to tell you how bad your situation sucks. Your marriage didn’t work out. I don’t know why yours didn’t last. There are only a hundred different reasons why. Maybe one of you cheated. Maybe you lost your attraction to your wife because she got fat and then didn’t want to have sex because she didn’t feel good about herself (one of my personal favorites). Could’ve been she lost her attraction to you because of your excessive gaming or love for sports, and lack of working. Hell, maybe you both just grew apart and it was nobody’s fault (yeah, yeah, sure). But now to your first date after divorce.

Regardless, you are now divorced, which means you are single again. Woo hoo! Time to enjoy being free to truly do what it is YOU want to do. It’s time to go on a date and it’s time to get laid. Now, this article isn’t about how to achieve getting that first date with someone. That’s gonna be tough for most, but eventually, you’ll figure it out and the day will come when you have a date with a woman who is not your wife. So let’s talk about how that will go.


Be excited. This is a milestone in getting past that dark storm you just weathered called divorce. This is your first date after divorce! You are going to be spending some one-on-one time with a female and that will involve a swirl of emotion. You’ll be excited and terrified, happy and sad, in the past and in the future, energetic and exhausted, wanting and not caring all at the same time. You are not used to dating so it won’t be easy at first. If you haven’t played baseball in years, this first date after divorce will be like your first game back and going to bat. Maybe you were a great hitter in the past, but chances are you’ll either ground out to first or just strike out the first time. Don’t worry about it. Just get through it and your next time at bat will be better.


I’m using the word successful here very loosely. Don’t be expecting to get laid. Chances are you are far from that at this point. Successful means you won’t make too many mistakes and it will end well, with you and her feeling good about the interaction. That’s all. Anything positive beyond that is purely a bonus. Here are some really basic things to help.

1 Dress nice – Call me Captain Obvious if you like, but this is very important and a lot of guys don’t pay attention to this. I don’t care where the date is or what the attire should be. Make sure what you wear is nice and makes you feel good. 

You may just be coming out of a hole that the nasty divorce put you in. Divorce is expensive so you may be kind of broke and haven’t bought any new clothes in a while. If you don’t have anything decent and up to date to wear to this date, then man the fuck up and go buy some clothes. And you may be used to your ex picking out your clothes for you. Guess what? You’re gonna have to go out and decide what is good for you without her. Do it and find more of who you really are without her influence. You’re single now and this is what single guys do.

2 Be clean – Males are allowed to be less put together and less clean physically. This probably started when we were little boys going out and playing in the dirt and not caring. When we would come home, mommy would wipe our noses and make us brush our teeth. It could be that you got married and your wife took over some of that mommy responsibility of keeping you tidy and clean. Wake up call: You’re a man now! That boyish attraction of having an untied shoe and a dirty face won’t work for you anymore. Most women are attracted to real men who are clean and together looking.

This new woman that your about to go on a date with isn’t your wife and may not appreciate that wild-looking beard of yours. Trim it up. And while you’re at trimming up or shaving your facial hair, consider a little manscaping to go with it. As we get older, hair grows less in some places and more in others. Do a quick check to see if you have any long hairs growing out of or on your ears. Check your nose hairs too. For years, I would painfully pluck each nose hair with tweezers until my eyes watered. I eventually couldn’t keep up, so I bought a nose trimmer that is painless and works well. Consider trimming down any overgrown patches on your arms and shave the hair in the back of your neck.

And make sure you at least don’t smell bad. Do the things necessary to smell nice by using whatever deodorants, body spray or oils, or maybe cologne. Also, do whatever it takes to have good breath. 

3 Make it a shorter outing – A first date should be more of an introduction. Don’t plan some full day of activities including dinner at the end like you’re planning on being partners in the Amazing Race or something. That’s a bad idea. Believe me. There will be time for all kinds of things if this first encounter is a success. Coffee for an hour or so is fine. Dinner is fine. A show is fine. But not all of them the first day.

You are dealing with single people now (unless the chick is married, but that’s for another article), and single people operate at all different speeds. Now, this first girl that you are going out with after your divorce may be your new soulmate and you both agree to get married by the end of the day. And if you can’t wait to do what Chris Rock says and, “Get back into Shawshank”, then cool for you bro. I’m sure forever will last longer this time.

As a general rule of thumb though, you want to slow the dating process down. There is a lot of desperation in the single world. Don’t feed into your or anyone else’s by starting with the first date being short and sweet.

4 Be polite and listen more than you talk – This girl might really like talkative bad boys and that may be you, but not on the first date. Don’t swear too much and ask plenty of questions about her. After you ask her a question, close your mouth and listen. Remember that this is only your first date. Success here means not making mistakes and the more you open your mouth, the greater the chance of a mistake. Let her talk. She’ll love it.

Almost one hundred percent of women like a little harmless mystery. I’m not saying to play some game here (unless that is who you are). Just limit her discovery of who you are and keep the conversation mainly on her favorite topic, herself.

5 Avoid incendiary topics like religion or politics – You may be really passionate about something that a lot of people disagree with you on. That’s ok. Just don’t get into a heated discussion on this first date. It may not go well. Women don’t want to hear a bunch of negative shit. Keep the topics positive, light and fluffy. There will be plenty of time to delve into your deepest and darkest opinions after this first date. Remember that success here only means NOT MAKING MISTAKES. This is your only goal.

Please keep in mind that this is your first date. I’m not suggesting that you not be who you are. It’s just that if you are an asshole, it’s a good idea to not reveal that too much in the beginning. Some woman somewhere may love your brand of asshole. But that same woman will decide you are not for her if you expose too much of yourself in the first parts of the relationship. This is human nature and we all do it.

Acting on our best behavior at first isn’t something evil like setting a trap or something. Getting to know someone is a process and should be. Acceptance takes time for everyone. Taking the stance that people need to accept who you really are, even in the beginning, is noble. Plan on being alone with your nobility and not getting laid much though. You’ll see this stance with some of the women you will encounter in the single world. They will be alone and not getting laid much either.

6 Do not talk about your ex – This is a big one! You are on a date here with a woman. She doesn’t want to hear about how you got fucked over by your ex-wife. You can talk about your past some, but leave your ex out of it. If your date asked you about her, give a short answer, make it positive, and direct the convo elsewhere. You didn’t go out with her because you wanted to have a session with Dr. Phil. You may eventually want to have sex with this woman. Don’t fuck that chance up by talking about your old witch of an ex-wife.

Women pay attention to every detail when assessing a guy. Every little thing carries meaning so if you have anything at all to say about your ex, express only a positive indifference towards her and your recent past. This new girl will be looking for you to say negative things about your ex and will build negative points against you if you do. That doesn’t mean she’s a bitch too or anything. She’s just being a woman and that’s what they do.

I’m not saying to be a closed-off person about things that you are going through. It’s just that your recent past (divorce) is not yet any of this date’s business. It may be in four or five dates from now when you are sleeping together and starting to become much better acquainted. Then, if you want, you can tell this new person how much of a cunt your ex was and is.

7 Be positive and fun – You and this girl are going on a date to have some fun and hang with the opposite sex a little. Don’t add any agendas to this first meeting. Allow this new person to enjoy who you are by not judging any part of her, you, or the experience. You will then be able to enjoy whatever she is offering you on this date. Try to smile, laugh, and have fun and try to have her do and feel the same.

You have the rest of your life to be serious about shit. Keep this date light and fun.

8 Talk more about the future than the past – It doesn’t matter if you are 18 or 89 years old. When getting to know someone, talk more about what’s in front of you than what is behind you!

I first learned this years ago from my karate sensei, Shihan Art Rott. When I first met him, he was in his mid-seventies and everyone who met and knew him loved him including me. Now, this guy had lived an amazing life and he had hundreds of great stories from his past that were entertaining and revealing to what kind of man he was. Shihan always talked about the future though, especially in the beginning. I didn’t start hearing about his interesting past until I got to know him better. Or I should say, “until he got to know me better”.

Single people live more in the present and focus more on the future than married or long-term committed people do. Don’t go on this date and remind her of when she visits her parents and sits with them talking about what is and what has been. Talk more about the present and future and only sprinkle in a story from your past. 

Talking more about the future than the past keeps a forward motion to this new relationship. This may be the only date you ever go one with this person, but that doesn’t matter much here. You are single now and need to focus on your future more. Your past life is over so this first date should be a reflection of that.

9 Don’t be cheap – You may be a frugal guy who is good with money. Hey, good for you man! When dating though, you can’t be cheap.

There are plenty of women out there who have no issues with their guy being a cheap ass. Not in the beginning though. At the beginning of dating, one of those same girls will label you as cheap and you won’t see her again. Seriously, in the beginning, being cheap is the same as smelling funny. Not good.

Don’t get me wrong here. I’m not saying to spend a lot on this first date. Spending too much while dating someone can set a very dangerous precedent for the future of the relationship. Just like there are many women who like frugal, there are many others looking for a male meal ticket. Don’t do the opposite here and set yourself up for a financial heartbreak by trying to impress some chick with a fancy experience and expensive gifts. Unless of course you are a baller and that’s how you roll. 

For this first date, pick a place that is moderately priced for who you are and your income level and then be cool with whatever she orders. If she picks a place and it’s more expensive than what you are accustomed to, then decide whether you want to go or not as she may have a higher lifestyle than you have and you don’t want that. If you choose to go anyway, then man up and don’t be cheap.

10 Be a man – Think I’m being Captain Obvious again? I’m not. Guys make this mistake all the time. Do the simple things like opening the door for her (maybe) and letting her go in first(definitely). Wait for her to sit before you do. Try not to be as sensitive as her and by all means, pick up the fucking check! Maybe you are broke. Tough shit. Pay for everything on this first date.

Note: I have noticed that some guys of younger generations are ok and even expectant for the girl to pick up the check. Some guys think it’s best and fair for both parties to split the cost of the date. If this is you, then that is ok. Be you if that works and is who you are. Just know that allowing or expecting a female to pick up the check is not at all manly. 

Depending on the woman your on a date with, you may not have to act much like a man and she will be ok with it. But this first date is more about you and not her. If you weren’t as much of a man to your ex-wife, then now is the time and chance to start being more of a man. So quite justifying acting like a girl. Man the fuck up and pick up the fucking check.

11 Have an alcoholic beverage or two. But that’s it – Don’t get me wrong. I think alcohol can be very important during the courting process, especially if you’re wanting to have some sex. This is your very first date after divorce, though, so don’t get drunk. Again, the goal here is only to NOT MAKE MISTAKES. If things go well here, the second date may have a lot of alcohol and a lot of sex. You may never get there, though, if you fuck it up in the beginning.

The date may go south for one reason or another. When it does, you may say “fuck it” and start drinking heavily. I don’t recommend this. Sure, the date didn’t work out, but you are in learning mode here. Be cool and respectful and end the date instead. If you still want to, go somewhere else and get hammered if you like. Just don’t do it on this date.


It’s not a mystery to any of us. We know how to act as our better selves. Most of us just choose not to act as well as we can because its work and we are lazy. This article gave a good amount of specific direction and suggestions. In the end though, you only have to be your better self on this date. Success is rarely a mistake or from luck. If you want to succeed at being single, you’re gonna have to work for it. And this first date is where the work begins.

If you are reading this and about to take your first date, I am truly excited for you. I was there once, as were millions of other guys. I’m also nervous for you, but you’ll figure it out and eventually be back to hitting triples and home runs with the bases loaded if that’s your thing. Good Luck!

One Response

  1. Earline Hogle April 13, 2020

Leave a Reply