How to Deal With Dating Disappointments

How to Deal With Dating Disappointments

In the summer of 2015 I decided to get serious about dating. I have the typical type-A “go big or go home” personality, and when I commit to something I’m determined to succeed. So I embarked on what can only be described as a dating rampage.

This intense focus on dating has been positive in so many ways. I’ve met a handful of great guys, have learnt so much about myself in the process, and collected an endless supply of entertaining stories to share with my friends. But there have also been many lows. And as a result I’ve had to learn how to deal with dating disappointments.

I’m in no way bullet-proof, but I’m getting better at bouncing back when things don’t go the way I expected them to. And here are four things I always try to remember…


Don’t Take Setbacks Personally

We’ve all been there: you have a handful of dates with someone, and everything seems to be going well. But then, all of a sudden, they vanish into thin air and stop responding to your messages. It can feel frustrating, heartbreaking, rage-inducing and confusing all at once. But the most important thing to remember is it’s not a reflection of you, and is always linked to that person’s own bulls**t.

There could be so many reasons why someone decides not to pursue a relationship. It just sucks when they don’t communicate that message properly. However, we’ve all been there, including Aziz Ansari who writes about being ghosted in his epic book, Modern Romance:

“A few months after the Tanya situation, I ran into her again. We had a lot of fun together and she eventually told me that she was sorry she didn’t get back to me that time. Apparently at the time she was questioning her entire sexual identity and was trying to figure out if she was a lesbian. Well, that was definitely not a theory that crossed my mind.”

So remember, it’s not you. It’s them.


Find the Humour in the Situation

As any single ladies out there will know, dating is completely exhausting. It should be fun, but the male population seem to be determined to create as many WTF moments as possible. And they’re doing a fantastic job. Really, well done guys, I applaud your commitment to the douchebag cause!

So the only thing you can do is find the humour in the situation. I’ve had my fair share of bizarre and perplexing moments – including a guy whose opening message on Tinder was, “Are your feet as big in real life as they look in photos?” I didn’t respond to that message, but I did screengrab it for future giggles.


Let Go of Expectations

First of all let me just say my personal expectations when it comes to dating are particularly low. I’m mostly just looking for someone nice, who showers daily and is reliable. But it’s disturbingly difficult to find someone who meets even these basic requirements.

Anyway, The Glitter Guide recently published a beautiful piece written by Kara Stout about her experience dealing with infertility. And this particular paragraph about letting go of expectations also applies to the disappointment you might feel when a relationship doesn’t work out:

“Having unmet expectations gets me every time. I’m working on this. I have to let go, I have to accept when things don’t go according to my plan or timeline, and I have to make an effort to still be happy regardless of these circumstances. Don’t get me wrong. I allow myself to cry and be sad. It’s OK to be heartbroken, it’s OK to cry and not want to get out of bed for a day. Allow yourself those emotions. But, I encourage you to then take the steps you need to move forward in hope again. A good friend once said to me that instead of considering when it’s the best timing for me, consider the timing of when the child is supposed to come into this world, the friends he/she will make, the schools, the time period they are supposed to be on this earth. This, for me, helped a lot in accepting that it’s just not my time.” [source]


Remember it’s all Valuable Research

Last fall I had the pleasure of spending some time with podcaster Jess Lively, and she said something so wise about dating that I’ve since repeated to all of my single friends. Dating is just data collecting. Yes, 99% of the time it feels like your efforts aren’t being rewarded. And sure, it’s really disappointing when you have high hopes for a date and it falls flat. But, at the end of the day, it’s all research. And each person you date will help to paint a clearer picture of what you really want.

Case point: last year I went out with a super-chilled surfer with long hair on the spur of the moment. He was so far from what I considered to be my “type” but I had a great time with him. We didn’t move beyond the first date, but that experience was so valuable because it encouraged me to connect with similar guys who I would have previously overlooked. So brush yourself off, get back out there and start collecting that data…

Have you had your fair share of dating disappointments lately? How do you bounce back and get back out there? Leave a comment below to share your thoughts…

P.S. Is it a mistake to always date your type? And the 7 dos and don’ts of online dating.


  1. This post made me giggle, and I so get what you’re saying! Big nods to the exhausting and perplexing. I’ve definitely found that moving on quickly and not over analysing situations with guys (who, in the end, I barely know) is the best way forward. Love the Lively quote! xxx

    • cocos_tea_party says:

      I totally agree – moving on quickly and not over analysing things is so important. Although, I’ve found every now and then, one complete moron will work his way into my world and create a heap of “WTF was that?!” over-analysis which I really resent haha. xxx

  2. And even if meeting someone… iffy does not teach us anything about things we might like, it gives a great insight into things we DEFINITELY don’t and next time we can spot them from far far away 😉


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