5 Awkward Dating Stories: Why?!

5 Awkward Dating Stories: Why?!

Nov 19, 2017 6 Comments

Are you aware of the lines “try and try until you succeed” and “select and collect”? To get to your goal of marrying your ideal man and your best friend for eternity you gotta go through some hurdles in the dating world. I have been in numerous dates with numerous guys. Let’s not lie here, it has been fun.  Back in high school, I never thought of myself as an attractive girl. I had a weird hair cut, my skin wasn’t that good, and my fashion sense wasn’t the best. Overall, I was just an awkward young lady.

During my high school years I dated about 4 boys and several flings. It wasn’t such a high school love story like we see in the movies. It was soooo boring.

Now we are going to talk about brrrr….. the most awkward dates that I had during my single life. We’ve all been there, I hope we’ve ALL been there. I know most of my friends also had these uh-oh dating moments and we love to share these to each other, laugh about it, and then tease each other about it.

So let’s meet four of those men in my past life:

Lost in Translation

When I was in the Netherlands I had a date with this Italian guy just because he was Italian. Italians left a great impression on me back in Italia so I just had to go out with one at least for a night in a country filled with Dutch men. Boy, it was a wrong move. We met up a bar in Amsterdam, ordered some drinks and tried to talk. We really really tried to talk, but there was just no spark for the both of us. Usually I have so much things to say and ask, but with him I was just speechless. I was just not into him. He would say something and I would not be able to reply anything afterwards and vice versa. Yikes.

I started multitasking and sending other messages to other guys to come and save me. Long story short, one wanted to pick me up so I had to tell this Italian that he has to leave now before he sees that I was meeting another! Oh boy.

A Blast From The Past

I never imagined myself being with one of my exes again until I met this guy who looked exactly like him in person. I was smitten by his charm and personality, but I wasn’t just so into it. You know the type of feeling where you don’t want to take the date seriously, because you just don’t want to commit. The date was great, he was almost perfect for me but in my head it couldn’t happen because I was leaving for Europe and I had to just be on my own and not be mentally and emotionally committed to anyone.

It was almost so perfect for the night until he confesses that he likes me and wants to take it to the next level. Uh-oh. I just had to turn break him a little bit right away, and told him that I wasn’t ready for any long term. He took it well because he didn’t want to go home, then we moved to another bar and he was such an awkward gentleman because every time he wanted to touch me and kiss me he would ask permission. Haha! Yes, a gentleman and not a loser.

We parted our ways and at the end I asked him, “What was your name again?”

Awkward Dating in Milan

Meet the Parents

An Italian man with a sports car took me out for dinner. Later he wanted to bring me to his house to hang out more and meet his dog… not only did I meet the dog but his parents too. Talk about awkward. Apparently it is quite common among adult Italians to still live with their parents.

The Gift Giver That Got Away

One of the guys I had a date with is an expat in one of these first world Asian countries. He is rich. He has indeed told me that he liked to shower the girls he dates with gifts, and surely I had no problem with that. Who doesn’t like presents? He flew all the way to the Philippines to be with me for a few days, brought me out for shopping, was even close in buying me designer brands such as Prada and Bottega Veneta (but I said no, I was being humble), and even got a table for me and my friends in one of the hottest clubs in the metro.

When it was time for him to go back home and go to work on Monday, I never heard from him anymore. A few months later he started dating another girl and got married soon. Turns out, the man was looking for a wife! Probably I wasn’t him for him, and thank the Universe that I am not. But grrr… I should have said yes to the Prada and Bottega Veneta!


For me it isn’t a date, for them it was so I’ll just include it here. 

It happened twice. It wasn’t considered a date in the first place. Mamma mia! Back when I was single and traveling alone, I used to do a lot of Courchsurfing in able for me to save money and meet new people while traveling. I met up with two Italian couchsurfers in Milan both in different events as I genuinely just want to taste home cooked Italian dishes. I did taste them and they were very very good.

However, these two seemed to wanted more. Obviously I was a female alone with them in their homes. I politely declined and suggested to leave after dinner before things turn ugly. Both of them kept asking why, I said, “Look, today what we’re doing is purely for the sake of cultural exchange. I did not meet you in a dating app, so please, this is not what you think it is.” They both had a hart time processing the logic out of it, and I also had a hard time why’d they think something so malicious from this.

Any awkward dating experiences you would like to share? I’ll prepare my pretend moscato and put my feet up while I read away!

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  1. Heather LeGuilloux

    Eek those are some scary dating stories! Hopefully you can look back on these experiences and laugh now.

  2. Omg thank you for your candor! This was a super fun post to read. I thought my dating stories were bad but I see now, they only touch the surface. Lessons learned make warriors!

  3. This was fun to read although I’m sure the experience wasn’t as fun! I haven’t had any crazy dates but there is always a lesson to be learnt!

  4. Wow! Dating is crazy isn’t it? But at least you got some good blog posts out of it

  5. Those are very awkward stories! But I’m sure you learned something from them all lol


  6. This was so interesting to read girl. Some parts like meeting the dog and parents brought me memories 😆. Thanks for sharing your experiences!

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