Dressing for Darkness: My Match.com Date From Hell

After a few failed Tinder dates (read about one of them here), I decided to step my game up with a little Match.com action. I thought that Match.com was a reputable site filled with men who were ready to date. Silly me. Match.com has been the worst performer yet when it comes to my dating career. Match.com is where the world’s biggest weirdo’s come to settle down.

Match.com sucks.


My worst date ever came from Match and also kicked off my “break” from dating. I should have known this particular date was doomed from the start. Why? I felt completely uninspired to choose an outfit (that never happens to me), and I ended up wearing a lackluster all black ensemble.

Let’s relive this nightmare, shall we?

The Man:

I’ll start by saying this; most of the men who message me on Match are either:

A.) Older than my Dad

B.) Have none of the qualities I stated I was looking for in a match

C.) Are hideous trolls (oh c’mon, looks do matter when it comes to online dating)

D.) Or they don’t even live in the state of California

So when this 40-something man with a nice physique, a sexy armful tattoos, a decent job, and what appeared to be a sense of humor, messaged me – I was game for a date. Yes, that was enough to qualify for a date with me. Match.com tends lower your standards without your consent.

We exchanged a few messages where he stated that he’d love to show me around Culver City where he recently bought a home. Now, in my opinion, a quality man comes to you, but since he seamlessly worked it into the conversation, I reluctantly agreed.

What can I say? The tattoos got me.

The Look:

The date was set for a Saturday night after I had worked a 12-hour-day teaching classes at my fashion school, School of Style. I had been on my feet all day and was so not in the mood for a date, but the date was set, and this could be the man of my dreams, right?

date outfit

I rushed home, took a shower, and started getting dressed. Was I to go with a dress or my deadly combination of a crop top and a pencil skirt? As I tried on outfit after outfit, I started to get annoyed with my date. Is this fool seriously making me drive to Culver City after I’d been working ALL day? This lack of consideration certainly didn’t deserve a skirt. So I opted for a new silk Rag & Bone racer back tank, leather skinny jeans, and Louboutin’s. Good enough.

Oh yeah, that’s me getting ready for this hellacious date.

The Date:

The date was set for 8:30 and I hate being late so I timed my drive so I’d get there at 8:15. I pull into downtown Culver City, and I get a text from Mr. Tattoo. He’s running late, can we make it 8:45?

Seriously, fucker? You LIVE in Culver City!! How are you running late?? I calm myself down; people run late – it’s okay.

It’s 8:35 and I am standing in front of the restaurant, which has an open front (you can see the outside area from the restaurant), waiting. Call me old-fashioned or crazy, but I feel like your date should walk in with you.  So I’m waiting, and waiting, and waiting. It’s 8:50. I decide to walk inside.

Jackass is sitting at the bar WATCHING me wait outside – this isn’t good.

We greet each other with a hug, and he looks nothing like his profile picture. The tattooed hottie was a gray-haired man with a Mohawk.  Not only were his looks not up to par; but he was also super rude!

How rude? This rude:

1.) He talked the ENTIRE time, and when I did manage to slip a word in, he literally turned away and started talking to his “friend” the bartender.

2.) Our date (after I had worked all day – he knew this) was all drinks and no dinner. Mind you I don’t drink. He also knew this.

3.) His “friend” the bartender called me Miss Boring because I don’t drink.

4.) Mr. Tattoo needed me to run an “errand “ with him, aka watch him give another bartender a mystery envelope.

5.) Some drunken blonde bimbo friend of his crashed our date where he went on to introduce me as a “Lauren, the teacher.”

Needless to say, I excused myself from this date almost immediately after it started.  Oh and he dare try to kiss me at the end of the night.

The good news it, a friend of mine called me right after and asked if I was wearing all black. I said yes (because I was). He said perfect; you’re on the list for a party, and you can only get in if you dressed in black.

Boom! I thought to dress in all black for a date, in this case, was simply dressing for my own dating funeral, BUT my wardrobe choice paid off in the end.

Takeaway Style Tips:

I’ll admit, I wasn’t a shining example of style on this date because I simply didn’t give a #*$%. It clearly didn’t matter because this guy was a total dud, but what if he wasn’t?

1.) Bring a backup piece of flash

I wore an all black outfit that was stylish (I can’t help myself) but I didn’t feel very special. Quick fix? Bring a special looking jacket or vest to throw on over your boring all black outfit.


2.) Rock some sexy heels!

My Louboutin’s took my simple outfit to a date-worthy outfit. Always wear shoes that make you feel sexy on a date, always! I went on one date where I wore flats because I walked to the restaurant; wish I hadn’t done that because I didn’t feel my very best.


3.) Make sure your makeup is on point

My face was winning on this date for sure. When you opt for an outfit that isn’t sexy-sexy or totally date-worthy, then you want your hair and makeup game to be on and cracking.

One thought on “Dressing for Darkness: My Match.com Date From Hell”

  1. That guy sounds like a first class d-bag… he was probably trying to get you drunk so he could take advantage of you. Good thing your friend came through with better plans!

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