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5 Tips On How To Start Dating After Divorce

April 09, 2021
5 Tips On How To Start Dating After Divorce

5 Tips On How To Start Dating After Divorce

If you have recently separated from your spouse, dating after divorce might seem like a daunting prospect. You might feel out of place, out of practice, and out of confidence. But everyone deserves that someone special so my advice as a dating coach, is don’t avoid dating. Learn how to start dating after your divorce to overcome the fear and build your confidence back up. 

Dating After Your Divorce In 2021

If you have been married for a while or out of the dating scene for a while, you might find that it has moved on quite a bit from what you remember. But that doesn’t mean that you can’t embrace it. 

The whole world of swiping and texting might feel like whole new world. Back in the olden days, before we were married, we met people out in the world– by chance or through friends. Thinking about the actual part about meeting someone online, after being married for so many years, might feel intimidating, exciting, but mostly, straight-up terrifying. But dating after divorce doesn’t have to be terrifying. It can be a lot of fun.

5 Tips On How To Start Dating After Divorce

How To Date After Divorce

After separating from my husband of 18 years, and moving into my own place, it took me about 30 seconds to put up a dating profile. Ok, maybe that’s a slight exaggeration. But I was eager to get out there! 

Talk Online

After putting up a meager profile at first, I matched with someone. We texted and talked for over a week before being able to go on an actual date. I felt relatively comfortable the few times we chatted on the phone. However, when I woke up the morning of the day of my first date, I was fraught with emotion. I paced around my apartment fretting about imaginary reasons why I shouldn’t be doing this. 

Don’t Make Excuses

I spent way too much time getting ready (and we were just meeting for coffee in the middle of a Saturday) and then tried to get out of it by making up a lame last-minute excuse. He saw right through it and called me and convinced me he was a good person who was in my shoes just six months before this. I hung up the phone having agreed that I would still meet him. I promptly called my best friend and told her how I had just lied to this poor man and there was no way I was getting myself out the door of my apartment. Luckily, she was able to talk me off the ledge and onto the subway to meet him. 

Just Be Yourself

Other than word vomiting through the first 15 minutes of the date, it went fairly well all things considered. I didn’t trip and fall. I didn’t spill my coffee on myself. And I didn’t get food on my face. We left one another on the street and I was uncertain whether I’d see him again. I just felt relieved to have ripped off the Bandaid of my first date with someone I met online. My date texted me later that day to tell me he enjoyed meeting me and asking if I wanted to go out again. I pulled it off. He actually wanted to see me again. I was crushing this dating thing!

Keep Your Online Dating Profile Updated

Over the next many months, I edited and reedited my dating profile a dozen times. It took me several virtual versions of an online profile before I felt I had one that conveyed the true me to potential dates. To my benefit, I was coming from the fashion and photography world so I know what looks good and what doesn’t look good in a photo and what to wear on a date. After some trial and error, I started attracting the right people for me, not just through my photos but my bio as well (contrary to popular belief, people do read them!). 


A little over two years later, I met my partner of four years on Tinder. I am a true believer that online dating can and does work. With a great profile and some perseverance, it is possible to meet your perfect match online. And I created a business helping others present themselves in the world of online dating the best that they can. Through revamping your wardrobe, editing and helping select the best photos, writing a perfect attention-grabbing bio, and being your cheerleader through the initial stages of dating. 

5 Tips For Dating After Divorce

From working with hundreds of clients and seeing thousands of dating profiles, I can tell you my top 5 pieces of advice: 

  1. Don’t believe in first date “chemistry” 

How many times have you heard a friend gush to you about how amazing the chemistry was on a first date… and the next time you see your friend and ask about it, they sheepishly say they never heard from the person again? It took me four dates before I realized there was anything but a friendship between me and my current partner. 

  1. Don’t be a dating dabbler

When my single friends say things like I was “lucky” to have met my boyfriend online, it frustates me quite a lot. I wasn’t lucky, I was diligent! It happened because I went out on nearly one hundred dates, with all types of people, from all different careers and countries and backgrounds. I took breaks when I needed to but got back out there again and again. 

  1. Don’t wait for other people to ask you out

This might take practice, but eventually you will get comfortable doing so. It took me a while to get there but the more confident I got, and the more experience with online dating I had, the easier it was. Many people are new to this just like you are and are just as nervous. Making the first move may be a relief to them!

  1. Practice taking photos of yourself

Like other things about dating after divorce, you have to get comfortable with having your photo taken and maybe even taking some selfies. I had almost zero photos of myself without my ex or my kids. I had to remind myself to have friends take photos when we were out to dinner or even out for a hike. You will like some photos and hate others. But you will get better at it! Like mom always said, Practice makes perfect.

  1. Have fun

Possibly my biggest piece of advice of all, is to not overthink online dating and enjoy your newfound freedom. Try to see dating as a way to connect with new people and find your youthful, fun side again.

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Alyssa Dineen

More About Alyssa Dinnen

Alyssa Dineen has been a fashion editor, stylist, and art director in New York for over 20 years. After she divorced at age 41, she began online dating, and rediscovered herself in the process. Through this journey, she found many people out there that could improve their dating profiles and while doing so, their understanding of what they want.