Before meeting Alena, I had my fair share of dates.  Many were fun, awesome, and led to good relationships.  And some…were bizarre.  Below are the ten craziest dates that I’ve had:

1.  The Wedding Ring
How we met: At a friend’s Ugly Sweater holiday party.  Just for fun, my wingman and close friend Eric (who looks nothing like me) and I told all the girls there that were stepbrothers.  Eric knew how to play the part since he actually had a stepbrother.  We improvised a story about how our parents met when we were in soccer practice.  There were two girls there that were fascinated with our story, and we ended going on a double date together.  

The date:  It was awkward, but awesome.  My ‘stepbrother’ Eric and I took the girls for sushi at KAZ Sushi Bistro.  In the middle of dinner, we broke the news that we actually weren’t stepbrothers, just good friends, and suddenly, there was an awkward silence, followed by nervous laughter.  Eric’s date was in the middle of a bite of sushi when we broke the news, and she couldn’t finish chewing it for at least two minutes after we told them.  We thought the date was going to be over soon, but it turns out that they didn’t care.  We ended up making out with them at the indie bar, Science Club, later that night.  Eric didn’t want the night to end, and actually said "I don't want this night to end" to his date (Tip: this line never works, gents. I’ve tried it.).  The bizarre thing was not so much the date, but what happened the next day.  My date was completely enamored.  She texted me 30 times and kept talking about her sister’s wedding rings and was hinting at the wedding ring she wanted - after the first date. It was all flattering but a bit too intense, and I had to let her down gently.
2. The ‘So Innocent I felt Guilty’ Girl
How we met: eHarmony
The date:  It was Spring.  We met up at the Smithsonian Castle, checked out the Cherry Blossoms at the Tidal Basin, and then went to the famous rooftop bar at the W hotel.  It was a great plan for a first date, but it turned out that the girl was just too innocent.  She worked at the Franciscan monastery.  I was the first person she ever had a date with, held hands with, and kissed.  She was 23.  She was a very nice girl, but we just had too many differences.  She didn’t like gay people and was a huge supporter of Rick Santorum.  I thought she was kidding.  I just couldn’t date her again. 
 
Right after I dated the world’s most innocent girl….I dated…


3. The Red Flag
How we met: A house party

The date: She ran marathons and did charitable work, so I thought that there would be potential.  After a few dates, she crossed off almost all the items in my dealbreaker list.  She smoked and drank often, ate fast food and McDonalds almost daily, slept with another guy while we were dating and told me about it, and had wild moodswings.  We went out for a weekday happy hour and she ordered 9 glasses of wine, costing $70.  I gave it a couple of months, thinking that perhaps things would change, but after I ran up the limit of my credit card, they didn’t.  Tip: You can’t change people. Take them as they are or move on.

4. The Free Meal
How we met: Speed dating
The date:  We decided to meet for coffee at 4pm at popular brunch spot, Founding Farmers, in DC.  I thought 3pm was a good time to meet to avoid a long awkward meal at a first date – most people have had lunch by 3pm, and it’s well before dinner.  It turns out that the second we sat down, she told me that she didn’t eat all day, and she ended up ordering 2 appetizers, one entrée, one dessert, 3 mimosas and a bloody mary.  I was shocked.  I ordered a cup of tea.  The total bill: $75.  She did not offer to pay.  After the date was over, she rushed out of there and hopped into a cab, never to be seen again.  That was the first and last time I was on a date with someone who was in it just for the meal.

5. The Furniture Snob
How we met: Speed dating
The date: We went on a few dates that went well, and eventually she visited my apartment.  A few days after she visited, she broke things off because she said that she didn’t like my furniture.  At the time, I was barely into my mid-20s.  All I could afford was IKEA furniture and a few hand me downs.

6. The Awkward Biter
How we met: eHarmony
The date: We met at the National Portrait Gallery and then I took her to a fancy chocolate restaurant in DC called Co Co Sala.  The conversation was a bit awkward from the start.  At the museum, when people were talking quietly out of respect, she kept talking very loudly about how much she wanted to marry someone rich so she could stop working and how much she hated religious people.  When we got to Co Co Sala, and I went in for a kiss, she went for a strong bite on my lip, causing it to bleed.  Worst kisser ever.  Needless to say, the date ended quickly after that.    


7. The Value-Add Girl
How we met: Speed dating
The date:  We went for coffee at Starbucks.  Off the bat, she told me sternly that she was a business operations consultant and is only interested in having dates that add value to her life.  I felt like I was in a meeting to discuss project management principles.  She didn’t smile at all.  Very un-sexy.  One and done.

8. The Narcissist
How we met
: At a meetup at Ultrabar DC

The date: My date was recovering from a bad breakup where she was dumped right before the wedding, and she was very anti-men when I met her.  She felt like other guys didn’t pay attention to her in the past, so she dominated the conversation.  She talked about herself, her career, her grad degree applications, her love of tarot cards and reiki, and her running all the time.  She barely asked me anything.  She was constantly fishing for compliments, and was way too self-centered.

9. The Runaway
How we met: At the Smithsonian American History museum.  We exchanged contact info but didn’t go out on a date until years later.
The date: She invited me to go for dim sum at Oriental East in Silver Spring, MD.  During the date, she was telling me how unhappy she was in DC (while I really loved it) and she was trying to move to Chicago as soon as possible.  Did she seriously expect me to just pack my bags and leave the city after a date? 


10. The Exhibitionist
How we met: Speed dating

The date: We went for Jazz in the Smithsonian Sculpture Garden, followed by drinks at Bar Louie. I asked her what she enjoys doing outside of work, and she tells me that “I enjoy being an exhibitionist and going to my BDSM club.  My ex-boyfriends would drive me to the highway. We would park on the side of the road, and I would get a thrill posing naked for pictures.”  I found it at first very intriguing, but as the date progressed, the mood was quickly killed when she freaked out when she couldn’t remember where she parked her car.  We walked around for two long hours looking for her car, and after we found it, she drove off.

Honorable Mention

11. The Cheater
How we met:
a few different girls I’ve met through speed dating, meetup, and eHarmony

The date: The dates I had with these girls weren’t bizarre.  It was the ending.  After one or two dates, I found out later that the girl I dated was still with their guy, had a recent fight, and are now getting back together with their guy.   


Final thoughts...
Everyone comes across a crazy date if they date long enough.  It’s part of the game.  And even though it can be a disaster at the moment, not everything is a loss.  It’s the disasters that make you recognize, appreciate, and hold onto the good one’s when they come along.  Six months after The Red Flag, I met my wife Alena at Ultrabar, and everything worked out.  Looking back now, we get a good laugh when we think of these dates.