23 – The First Boyfriend

The word got out fast that I was single and I guess guys deemed it acceptable to message me even if we hadn’t spoken in years… to re-connect they said. SUREEEEE! I was receiving these random messages from guys I knew but haven’t really spoken to in years. Obviously, there was Mr. Unfinished business who was still actively messaging me here and there to get a few naked pics of me so he could gladly masturbate on the thought of what could be…. and I gladly teased him – yes I am that nice… but there was one random Facebook messenger ding I was not excepting.

“I heard recently things havent been the easiest. This is me sending positive vibes”

I think I re-read that a good 10 times. Why was my first love, my first boyfriend messaging me on Facebook? I had not spoken / chatted with him in years… eight to be exact. The last conversation we had he was trying to convince me that I should really reconsider getting married. That life was short, that I had so much to experience and live. Sure now, I should of listened to his advice but at the time I thought the path I was taking was a good one, so I politely thanked him for his advice and did not speak to him since then. 

I loved this guy. With all my heart. My first love. I was 14 and he was 16 – an older boy and I was head over heels over him. You know the puppy eyes and the butterflies… he even called me from his New York trip to official ask me to be his girlfriend. I was in love. We dated 6 months… and when I told him I was ready to have sex, he dumped me. (who does that?!)


Yes – I was devastated – my plans for him to be my first went down the drain and he regrets that poor decision ever since (he admitted this YEARS ago – so if felt kinda nice) So you can understand that seeing him messaging me at 12:30 am on a Friday night made me think that he wanted to make up for lost time. Any girl would think that. I was curious… so I said fuck it and replied. 

“So I was thinking about it and if ever you want to catch up over drinks or coffee I’d love to”

He thought the idea of meeting up would be interesting (that was the exact word he used) yup, to chat about what we have done in the last 17 years and nothing more.  I didn’t want this to turn into a sex date (not right away anyway) and made that clear. He said I was nuts and he had no other intentions but to have coffee and chat. SUREEEEE! Guys always think about sex. Always. He asked that we text message instead because he wasn’t really into the whole Facebook Messenger thing (so yes, he went out of his way on a friday night to message me …. for coffee?! Nice one dude)  so I did just that…. and his response was a classic one …

“Hello Little Ms. Single”

Oh boy… does he think I’m stupid. I could already see his game plan and I was onboard but obviously didn’t tell him… I was looking forward to seeing how this whole coffee date would pan out. The date was set. A Monday… Two weeks from his initial message…


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