How to End a Relationship After the First Date


Every one of us has run into a colossally bad date at some point in our lives, and have thanked the Good Lord above and Mary our Blessed Mother when we were finally able to end the evening.

But sometimes these clueless dates don’t get the message when we simply say good night politely, and persist in trying to turn a debacle into an ongoing relationship.

Now, most people aren’t trying to be bad people.

Sometimes we just don’t click, such as the time an Italian-American gal I was seeing in Chicago decided to tell me that “sometimes you just know it’s not a good fit – it’s like a shoe.”

Now, while it was slightly upsetting to be compared to footwear, it wasn’t really worth the effort I made to plead my way into a follow-up date. The analogy worked wonders at making me realize that this Cinderella was determined to find her glass slipper from a completely different Prince Charming.

So how can you effectively end a ‘relationship’ after just one date?

I’ll give you a couple of examples of how I was given some pretty direct signs that things were not meant to be, and then save my dignity by sharing with you a story in which I was the one having to do the dumping.

Claim a medical emergency and leave them guessing if you’ve survived 

medical emergency

One Christmas season about a decade ago (how depressing – a decade!), a guy named George (especially himself) assured me was the matchmaker of my Los Angeles Catholic social scene offered to introduce me to two different women in one night at a Christmas party.

I went and met both of them, finding them both to be lovely personalities, attractive as well, and witty conversationalists, while they practically fought each other for turns to speak with me (trust me, I was as surprised as you are!)

While I wound up with both their phone numbers, the ensuing dates were not the dream matches I had presumed they would be.

On the afternoon before one date, I called the young lady to finalize details and she shrieked in a panic: “I can’t do this now!” before slamming the phone down.

I learned more than two years later that her exclamation was legitimate, for she had burst her appendix minutes before and was on her way to emergency surgery. But as we all know, God has a plan for us all.

Make no effort whatsoever to impress the other person, and blast through your encounter as quickly as humanly possible

bad date

I did make it to the other date, but for some reason she didn’t turn out to be the same as when we met, either. She kept asking me if we could “just eat at the restaurant in your building.” At that time, I lived in an apartment building with a built-in restaurant.

Since I was under the impression that going on a dinner date should involve actually going somewhere other than your home, I asked if we could in fact find another dining establishment.

She proceeded to halfheartedly point out that there were several restaurants “around the corner from you.”

I still felt like I deserved to ask for a place where we could get to know each other without the likelihood of my neighbors also discovering everything about us, so we finally wound up going to LA’s top Mexican restaurant, outside my neighborhood.

Yet she still wanted to see if we “could just meet at six.” Who does that on a Friday night?

I managed to push it to 6:30 but no further luck, and she arrived for our first date wearing overalls and pony tails, and no makeup.

She then plowed through dinner with only the smallest of small talk and managed to drop me home by 8:00.

On a Friday night.

It made me wonder if she had a second date to make it to, or if her overalls meant she had to hit the hay super early to go tend to some crops in the morning.

The point was made, though.

There would be no second date.

Don’t make a wedding your first date

beach wedding

Finally, I once took a potential romantic partner to a wedding. My guy pals warned me that weddings are to be reserved for serious girlfriends, but I thought why not and threw caution to the wind with the wedding as our first date. Since I didn’t vet her enough, I had no idea that she had been stood up at the altar herself just a couple months before.

This led to her weeping profusely throughout the ceremony, which made things awkward because everyone assumed I was making her cry rather than the memory of her ex-fiance, or that she was just crazy.

By the time we hit the reception elsewhere, she was heading for the bathroom to cry and not coming out anytime soon, so a mutual female friend told me to “just go ahead and do your thing.”

I wound up hitting the dance floor and I do have some great moves, so I quickly met the Italian-American woman I mentioned at the start of this column.

We danced the night away, and I left a legend among the men, as a guy who arrived with one date to a wedding, but left with another.

Yes, this is not normally appropriate wedding behavior.

But at the time, I had no real other options and our friend assured me she’d get my first date home safely.

Never make the first date a wedding. It’s just too much pressure.

Fate got me back later anyway, as I was kicked to the curb like an old shoe.

Share some of your disastrous first dates and how you managed to make sure there wasn’t a followup, in the comments below!