Divorcée and the City

Entering the World of Dating After Divorce

It’s been a few months or even years since your divorce finalized and you are wondering, “Is it the right time for me to date again? Am I really ready? What will people think?! How do I even get started? Will I feel safe while dating?” Let me help you to answer some of your questions, so you can courageously mingle with the singles.

If you feel that you’ve allowed yourself plenty of time to heal and move on from your former life as a wife, and now want to date, congratulations on taking this brave new step! It is really scary putting yourself out there after being with someone for so long, but this is an extremely exciting time too.

I was seventeen when I met my first husband and twenty-six when we called it quits. I had never really experienced dating before, unless you count high school “dates”. I had no idea if I was ready, how to begin, or what the best way to meet decent men was. I hadn’t been able to bump into the love of my life while reaching for the same melon at the grocery store, or while trying my hardest to look cute while pumping gas, so this was obviously going to take some work.

Am I Really Ready to Date?

You may be considering if it is the right time to start dating, but the honest truth is, there is no set timeline. Every person experiences divorce differently and each situation has it’s own unique healing process.

The biggest mistake I made after my first divorce, was trying to date when I hadn’t allowed myself the time to fully process and recover from that marriage ending. I began dating about 6 months after the divorce finalized, and in my situation, I probably should have waited for a couple of years.

At the time, I used dating as a band-aid for my bleeding heart, instead of approaching it for the right reasons. Although I thought I was being picky in my selection process, I really was rushing into another relationship because I thought it would make everything better.

I ended up with a man who checked most of the boxes on my list, but who I always questioned and never felt 100% right with. This led to marriage #2 and my second divorce after only a year.

Photo by Jeremy Bishop on Unsplash

In contrast to my first divorce, the second time around I found myself able to heal much more quickly. I’m not sure if this was due to the fact that it was my decision to divorce, if it was because I had already done it before, or because I wasn’t as deeply in love as I was the first time. Either way, I found myself relieved and much happier on my own.

I immediately decided I would never date again. I had no interest in falling in love, hurting someone else, or being hurt myself. I focused on my happiness, doing what I loved, and found this divorce experience to be completely different than the first one I endured.

Life has a funny way of ignoring our plans though, and VERY quickly after filing for divorce, I unintentionally met the most gorgeous and wonderful man ever to grace my life.

I was extremely resistant to getting into another rebound-type relationship again, trying not to take things too seriously. I even tried to walk away from him, as I felt that I would become attached and this would lead to more heartbreak. The connection we shared was far superior to my desire to protect myself, so as much as I tried to fight it, I found myself unable to.

2.5 years later we are still together, have an amazing son, and I haven’t felt more at peace in my life. I never question that we are supposed to be together or that I was ready for this relationship because it has felt right and destined since the second our eyes first met.

This just goes to show you that some of you may feel ready to date shortly after divorce, while others may need months or years to fully heal. Don’t feel pressured to get back out there, and don’t feel ashamed if you are ready faster than others deem appropriate. Only you know what you are feeling and experiencing, and only you will know if it is good timing or not.

Photo by noor Younis on Unsplash

Just look inside yourself and make sure that when you do decide to date, that you are doing it because you are ready to love someone, not because you need to be loved to heal your heart. FOLLOW YOUR GUT!!! This is the one thing I did not do after my first marriage failed, and I wish I wouldn’t have tried to force myself into something that my head thought was right for me, when my intuition was screaming for me to get out.

Now, on to the fun part, where to meet men…

The Sexy Bar Scene

Following my first divorce, I decided that the best place to test the waters of eligible bachelors was at bars. People meet at the bar all the time, right? It worked out perfectly for my best friend, who had met the love her life while out one night! It couldn’t be too hard; you just get dressed up, gather some girlfriends, and go out. Then while shaking your booty on the dance floor, your eyes lock with a sexy man across the room and boom, you’ve found someone to date.

Unfortunately, my experience of trying to find a boyfriend in the nightlife scene was quite unsuccessful (at least post divorce #1). My friends and I spent our weekends at local dance club bars, on the prowl for men. The sea of steamy, single men that I was expecting, was more like a pond of creepy toads trying to grind up on my lily pad. No thanks! One of my girlfriends did get lucky and met her husband while we were out dancing on New Year’s Eve though, so it is possible to find a prince among the toads.

When the dance clubs failed me, we went to dives, sports bars, and cocktail lounges, in hopes of connecting with less sketchy dudes. Once again, some of my friends found love, but I never made a real connection, until I wasn’t looking for one, during my second divorce.

I met my current boyfriend at my favorite neighborhood dive bar. A friend and I went out, just to catch up and spend time together. In walked the love of my life and sat across from us. Although I wasn’t seeking a relationship, I felt drawn to him and moved to sit next to him. I said “Hi” and we have been inseparable ever since.

That moment single-handedly changed the way I used to negatively view meeting men at the bar. It really is possible to meet good guys anywhere, it is just a matter of being at the right place at the right time.

Online Dating

I tried online dating after my first divorce. Keep in mind that this was well before Apps like Tinder were prevalent, so there was no swiping for men or quick hook-ups.

I will say that, overall, I found online dating to be a good experience, but it definitely led to a few odd moments as well. I really enjoyed “shopping” for a husband. I found that being able to narrow down the vast pool of men, to the people I thought I would actually click with was great!


  • If you don’t find someone’s profile appealing or you aren’t attracted to them, then you don’t have to talk to them. Easy as that!
  • You can block annoying or inappropriate people, unlike when they approach you in the bar and you have to say, “Go away”, to their face
  • Narrowing your search to people with the characteristics you are looking for
  • You choose the people you talk to
  • Conversing with potential partners and learning more about them before wasting time on dates
  • Finding the perfect person for you

Photo by Mimi Thian on Unsplash


  • Having people say rude things to you when you don’t respond to them, or turn them down for dates
  • Meeting crazy people
  • Unsolicited dick pics
  • It can be pricey
  • Time-consuming

The process of going on multiple discouraging dates can become tedious, but I have a plethora of humorous date stories, met some cool people, and had fun for the most part, so I would say it was worth it for me.

I did meet husband number two on Match.com. Even though that didn’t work out, I do believe that if you are ready, patient, and willing to put in work, you can find someone whom you are compatible with.

Getting Set-Up

It seems like once the divorce has finalized that friends, family, and acquaintances start crawling out of the woodwork with single friends who, “You just have to meet”!

I experienced this after my first divorce, and it is actually the reason I started dating long before I was really ready.

I was a daycare teacher at the time. News of my divorce was a hot topic of conversation in our gossipy little workplace, to the point where parents of my students were checking in to see if I was doing ok…awkward!

Even more awkwardly, I actually had a student’s mother ask to set me up. Apparently, her brother-in-law had seen our class photo hanging on the fridge and was interested in dating me. I had always believed in keeping personal and professional lives separate, so I politely turned down the offer to meet him.

She had asked me a couple more times and each time, I said no. Then she brought in his photo…and I said yes, Haha!

We went on a few dates and I discovered that he was a little more of a casual dater than I. He admitted to dating multiple women at the same time. Although that is fine, it wasn’t for me at that time, so I decided we weren’t a good fit and stopped seeing him. That was the only time I ever allowed someone to set me up on a date.

The main point I’d like to make about being set-up is, don’t feel pressured to say yes! If you aren’t ready, or you feel in your gut that it isn’t right for you, then be firm with your decision.

Being set-up can work for people, but I think it’s best reserved for those who know you very well.

It Always Happens When You Least Expect It

Have you heard this? It’s one of those phrases that really gets under the skin when you are lonely, impatient, and desperately wanting a partner…That being said, it’s kind of true.

Ok, I’m not expecting it today!! Universe, do you see that I’m over here, not expecting it?!

I had a very hard time with this concept during divorce #1. I wanted a relationship NOW. I didn’t want to wait until I didn’t want it. This is the exact mindset that is a dating red-flag. Feeling like you need a relationship in order to be happy, is a sign that you may not be ready.

I can see it now, how needing to date led me into another disappointing marriage, which resulted in more heartache. If I would have been patient and taken time to properly heal my heart, I could have saved myself a lot of drama.

The relationship I have now, came from loving myself. I found him when I wasn’t expecting it. I was in a great place. I loved my life and loved the person I had become. It was consciously making the decision to be alone and enjoy life as a single woman. I think that is what caught the universe’s attention. “Oh, you want to be single forever, huh? You’re happy and having fun? Well, too bad! Here’s the person you were always meant to be with, so just try to get out of this one.”

First Date Tips

It is possible that you’ve already found someone whom you are interested in going on a date with and are feeling nervous about what to expect. What are you two going to do? Who pays? What if I hate him/her?

1. Skip Dinner

Please, save yourself and don’t go to dinner! There is nothing more awkward than going to a restaurant with a stranger and finding that the conversation has stalled before the appetizers have arrived. The best piece of advice I have for first dates is don’t do something that requires you to stick around for a long period of time, just in case you end up detesting the person.

Meet for coffee, a drink, ice cream, or anything which allows for a quick exit if you aren’t feeling it. As long as you have ample time to assess your date and decide if you enjoy their company, that is all you really need. I always knew in the first five minutes whether or not there was a potential of compatibility or not. If you like the person, great, go have dinner or continue the night as you wish. If you know this isn’t the person for you, then thank them for their time and excuse yourself.

2. Bring Cash

I highly recommend bringing cash so you can pay for your drink and run, if necessary.

My first online date was a disaster, so if I had cash I would’ve laid it on the table and ran out. I was at least smart enough to have him meet me for a beer at a local brew pub, instead of doing dinner, thank God!

The first this I noticed was that when he showed up he didn’t look like his photos. This was when I learned the importance of seeing multiple photos of different angles: Straight on, up close, full body, not just selfies. Very quickly I knew I wasn’t interested in him.

After introducing ourselves, we ordered drinks…which he put on my bill!!! I was in such shock that I didn’t know how to respond. I always assumed that I should pay for myself, unless the other person offered, but I never would have expected someone to presumptuously put their drink on my tab.

Once I got past the initial shock, it only took him a matter of minutes to reveal that he was looking for a sugar mama, had a bladder disease which caused frequent urination, and was kicked out of high school for being such a trouble maker. Way to sell yourself dude! Where do I sign up?

3. Leave if you are uncomfortable or feel unsafe!!!

I snarkily explained to him that I was a teacher and planned to work with non-profits to help the impoverished community, so I was no sugar mama. I then asked why he hadn’t used the restroom if he had a bladder issue, which is when he excused himself to go pee. The second he was gone I asked for the bill, paid it, and literally ran out the door. The people around us must have heard our conversation, because they started laughing when they saw me running past and one woman even said, “You go, Girl!”

When I got home I blocked him from contacting me again.

4. Never Give Personal Information

There were a few dates I went on where I felt like the person had a screw or two loose. There was odd eye contact (I’m talking serial killer eye contact), weird questions, disrespectful talk of exes, and awkward attempts to make physical contact. I was happy that I had never exchanged last names, that we had met out, rather than having them pick me up, and that I hadn’t shared my social media profiles beforehand. There is no reason to give away too much about yourself before getting to know someone.

5. Make Sure Someone Knows Where You Are

Before going on dates I always made sure that my closest friends knew when I was going and where I was. I gave them all the information I had on the guy (screenshot photo, name, number, etc.) Within an hour, if my friends didn’t hear from me they would call to check in. I know this seems extreme, but it always made me feel safer.

Maybe I was just paranoid, but I think it is ALWAYS best to listen to your gut. Maybe the person isn’t a serial killer or rapist , but why risk putting yourself in a bad situation?

Never feel bad for leaving a date where you are not enjoying yourself, feel unsafe, or know with certainty that it isn’t going to lead to a lasting relationship! When we don’t listen to our intuition for fear of being rude, this is what leads us into uncomfortable and sometimes dangerous situations. It is much more rude to lead someone on. It’s not worth wasting your time, or the other person’s time when you know you aren’t interested. It is especially not worth your life, if you feel something is off with your date.

6. Have Fun!

There is no reason to be afraid of dating, when you take precautions. Most of the time, you are able to filter out the weirdos before you actually go on a date. If someone is acting obsessive, is going overboard with the flattery, is calling you pet names, or says they love you before even meeting you, run like hell! If you have a bad feeling just through chatting, then cut off communication.

Although I did meet some odd ducks, most of the men I met were actually cool guys, they were just not right for me. You shouldn’t put pressure on yourself by taking dating too seriously. Most of the dates I had were not with someone I wanted to spend my life with, but were enjoyable and were good company. Use dating as a learning experience, where you can get to know yourself better and find out what you want and don’t want in a partner. I had some really fun experiences, made funny memories, and discovered more about myself through dating.

Do What Makes You Happy

I’m not going to tell you when you will be ready or what will work for you, because I don’t know you. Even if I did, I’m not a psychic. So, if you know you are ready, then get out there. Date. Sometimes it works, other times you will find that you need more time, and that’s ok.

Not everyone wants to have a life partner. Divorce is draining and maybe you feel like you are happier on your own. Good for you, do what is best for you. The most important thing is that you are moving on with life and finding happiness, whether that is on your own or with someone new.

Good luck and may you find peace!

Love Always, Alex Prince – Creator & Editor-In-Chief of Damsel Divorcée

2 thoughts on “Divorcée and the City”

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s