Dating Dilemma: When He "Forgets His Wallet"

Even as an experienced dating coach, I can sometimes find myself in a situation. 

Trust me, over the years of being a coach I have heard some crazy stories.  And there’s no greater debate when I host live coed events than over who pays for first dates! 

I’ve met women who went on first dates with men who told them exactly what dollar amount they could order, brought coupons (which I’m all for on subsequent dates), refused to buy coffee, men who’ve been asked how much they make on a first date and more. 

But I hadn’t heard of the forgotten wallet ploy until it happened to me.

I met the Architect on OKCupid.  We had like a 97% match so it seemed worthwhile to start a conversation.  We had a few back and forth messages. Two days later on a Friday morning, he asked if I would like to get a drink that night. 

Generally, I like a phone call first and am not much for spontaneous dates.  However, I am always up for growing my comfort zone, so I said yes.  I had a lunch date that same day and figured I would already be in first date mindset, so why not? 

He wanted to meet at a swanky, upscale scotch bar.  

Being not much of a drinker, and hello―A WOMAN, I know nothing about scotch and asked my best guy friend RC about what to order.  He sarcastically said wine, which would have been good advice had they served anything other than scotch. 

I got there first and was waiting just inside where I could see people approaching.  I see him walk up staring with his phone.  He then makes a phone call before coming into the restaurant.  He walks in and tells me that he had just went to work out at the Y and left his wallet in the locker room.  He says he tried to call and no one  answered..only I saw him talking and pausing and talking again. 

Of course, if I thought I left my wallet where it could easily be taken, I would have been a little panicked.  I imagine most people would.

I suggested we just reschedule for another time because he needs to go and get it before someone else does.  He didn’t reply the way I would have thought. 

He asked if I would be willing to buy him a drink. 

When you are a dating coach, making you easily google-able, you live with the knowledge that if you give a bad first date that it would be easy for someone to write something bad about you.  

Therefore, I felt a little on the trapped side by his question.  If I had said “No” then it could have been twisted into me expecting a man to always foot the bill or not being fair. 

Instead, I said “Are you sure you don’t want to go rescue your wallet?”

Ushering me to the bar, he replied “Just one quick drink”

First off, as I’ve written before, I’m not a fan of Quickie First Dates.  Second, if I was going to initiate a date (and therefore pay for the whole thing), I would have done coffee or dinner.  Third, I don’t drink.  I never even finish a drink and certainly wouldn’t have picked a high-end scotch bar.  Finally, while I have always offered to pay on every first date I’ve been on, the man has always said “I’ve got this!” (Note—I insist on paying for subsequent dates.)

The conversation was just okay and not reflective of how we had so many common answers for the matching matrix that OKC uses. He said he owed me dinner or something because of the wallet thing but I somehow doubted his sincerity in that sentence.  Given the lack of good conversation and chemistry, there was no need for a second date. 

He ordered a Manhattan and finished it right away.  I had ordered a mule that had scotch instead of vodka and didn’t care much for the combination, so he asked if he could finish my drink, too! 

I wasn’t going to drink it, but that’s, as we like to say in the south…tacky!  

The bill came―$30 for two drinks—what a waste of money.  We could have had dinner for those prices. 

I paid the bill and we walked out.  I offered a quick hug in front of the restaurant.  He tried to kiss me, I gave him the cheek but he caught my lips for a quick peck on the way out of the hug. 

Then suddenly acted in a hurry to get to the Y to retrieve the wallet when he had barely mentioned it before.  You know…because chances are his wallet was in his car!  An hour or so later I get a text saying he had found it and how embarrassed he felt.  I never heard from him again. 

I texted RC about it and he said “Gosh, it sounds like he does this often…it’s kinda brilliant if you’re an asshole!”  

We then dialoged about what we would have done if we had been in his shoes. We both agreed we would have called the date and let them know we are going to be late because we have to go and get our wallet.  Then ask the date if they would like to wait for you or reschedule to meet another time. 

This is one time a quickie date was okay because he not only took advantage by stealing a kiss, but basically my drink, his drink and my kindness, too.

Going home with Thai takeout and my own company was a much better way to spend the evening.  What kind of Thai dish?  Drunken Noodles, of course!    

Let me hear from you….What would you do if you were the architect or me?