10 Ways Dating is Like Shopping For a New Wardrobe


1 – You know those items you bought because they represented who you want to be seen as or because they were marked on sale only to languish in the back of the closet because they never were really quite right? It’s easy to do with people too – to drift into a relationship because the person looks good on paper or because we’re afraid to pass up what seems like a good deal. But it doesn’t matter how many boxes they tick if you’re only going to take them out due to a sense of obligation.

2 – Do you have that special go-to outfit that you pull out whenever you need a jolt of confidence? Clothes have power – when it’s right it not only makes you look good, it makes you feel good too. Likewise, that’s a sign that you’ve landed on a compatible partner. The right person highlights your best attributes and minimizes your flaws.

3 – I used to have a pair of jeans that I absolutely loved. They hugged the curves in all the right places and yet still managed to be flexible enough to let me move. Those jeans are now rarely worn since my body had changed in the intervening years and the denim has not. Sometimes the fit can be altered, and sometimes it’s fixed. People are the same. You may find someone who is great fit for you now but may not be suitable down the road.

4 – The stores are always pushing the latest trends. Overwhelming the senses with eye-catching displays enticing you to buy something that will become irrelevant (and thus unwearable) within the year, encouraging you to open your wallet yet again. The wiser buyers resist this pull and instead head to the more sedate racks in the back where the timeless pieces can be found. All of that peacocking is also evident on the dating scene – the bright baubles and carefully arranged coiffing vying for our attention. When often we’re better off investing in the more boring and yet enduring ones.

5 – It can be a little unsettling to learn that the sweater you just purchased had been taken home by someone else. At first, you can’t help but think their presence, their flesh on the inside of your garment. But soon enough, it simply becomes your sweater with your scent and the imprint of your form starting to customize its shape. Similarly, it can be strange heading into dating when most of the people have been divorced – bought and returned, if you will. It’s easy to focus on where they’ve been. But as long as they’re still in good condition, their prior journeys will soon fade away.

6 – There’s a reason that the most exclusive stores are often the smallest – we become overwhelmed when presented with too many choices. Those enormous warehouse-styled stores with their endless racks provide endless opportunity and also endless discontentment. What if there’s a better choice in the next aisle? Dating has suffered the same fate. The friend of a friend has been replaced with technology-supported warehouses of endless options, the result of which can leave of paralyzed and unable to choose.

7 – Even though I know better, I still make the mistake sometimes. I commit to piece of clothing without taking the time to try it on. Only to discover that it doesn’t really fit right. And then I usually suck it up and keep it because, let’s face it, returning something is a hassle and can even be uncomfortable. It’s easy to make the same error in dating, to pledge loyalty to someone before really trying them on and then to hold on to them too long once the mismatch is discovered.

8 – I’m convinced that the people who design fitting room mirrors and lighting are sadists. I mean, I don’t really look like that, do I??? There is nothing like trying on clothing to make you feel insecure about yourself. Well, except dating, that is. Trying on anything brings out our inner doubt and feeds our self-judgement.

9 – Speaking of fitting rooms, they can begin to feel like jail cells built atop a treadmill, as you endless try on and discard items looking for the best fit. Fitting room fatigue is real. There’s a reason they always offer benches so that you can rest and find your second wind. Dating can be equally as tiring. Luckily, you can always find a place to rest for a bit.

10 – I loved that shirt. I mean, really loved it. I gave it a place of honor in my closet and washed it with such care for the first few months. It was special and I made sure to treat it that way. Yet in time, life seemed to speed up and one weekend, I carelessly tossed that once-precious shirt into the dryer, ruining it forever. Finding the right piece is only the beginning. You have to take care of it. When we stumble upon a new partner, the novelty and excitement of it all ensure attention. It’s on us to make sure that attention and care doesn’t fade.

Thank you for sharing!

12 thoughts on “10 Ways Dating is Like Shopping For a New Wardrobe

  1. I could not think about the fact that some of my clothes shopping is accomplished at the hardware store…the outdoor store is a close second.

  2. This one is so right on target! I love your analogies! Makes it sound much simpler. Yet I’ve still to go on a date(?)!! after all this time! I’m afraid I’ll scare someone to death with what I can’t stop my mouth from saying, & that’s just not fair to some unassuming man. I look so innocent!

    Patrick! I still have lots of his old carhart work clothing! He only came to get his stuff 542 times & never did get it all!
    (Bit exaggerated), but the cops with the escort always got a good show!

      1. I still can’t refrain myself either. 5+ years away from him with Zero contact and so many things that happen or come up that I instantly have a horror story come to mind. (stories you doubted yourself about at the time). Not until your world crashes down do these things make sense, and then the “Aha” moment.
        If my ex had not moved back near me, (worse yet within a mile of my grown daughter), with the gf who was our friend along with her now ex husband, it would be much easier. He managed to manipulate my daughter, (from my first marriage out of high school), into believing I’m cRaZy, I’d be much better emotionally. She and I were the closest always. Yet, he managed to convince her to hate me, and it’s now been nearly 5 years since seeing or speaking to her or my three beautiful granddaughters. She never even came to me and asked any questions of me. I’ve remained silent and heartbroken waiting for her to see what happened for herself because I know it’s got to be her that sees what he is.
        It’s by far the cruelest thing anyone could set out to do. The most devastating thing of all and I’m sure he’s smiling about it. It’s HARD to be strong most days.

  3. A Familiar Stranger – Middlesbrough, North East England – My name is Matthew Williams, single father to two wonderful children, making it up as I go along. I am a blogger and author. I started my blog, Love, Laughter & Truth, in December 2015 as I attempted to make sense of my rollercoaster life following depression, divorce, and my introduction to the weird world of dating. My first book, Something Changed: Stumbling Through Divorce, Dating & Depression, was published in paperback by Sixth Element Publishing in December 2017, and is available to buy on Amazon. You can find my writing at https://lovelaughtertruthblog.com/ I hope to see you there!. Very best wishes Matthew
    Love, Laughter & Truth says:

    This is a great post! Always love a good analogy and this works perfectly for dating 👍

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