Freaking men out by my boldness, one interaction at a time.

“You scare me a little bit with how direct you are, Ann,” the 54 year old creative type texted last night. “Remember, I write poetry.” Sigh. 

I didn’t have the heart to tell him I disliked most poetry: it’s not my thing. After our brief after-dinner drink last week, he’s been communicative and sweet. He told me he couldn’t stop thinking about me and felt like a teenager. But he’s too saccharine at times – he said I was a “little sweetheart”, two words I would ever use to describe myself.

We will see how the second date goes, when we get to it.


One of the contractors and I were supposed to meet last night. For a rough around the edges guy, he’d been remarkably responsive and kind. 

We aren’t soul mates, but over a shared platter of nachos we talked about astrological signs and his pet snakes (!) and I stared at his muscular hands and forearms.

We aren’t soul mates, but I’d fuck him.

We had plans for a second date drink in my neighbourhood. My plan was to have a couple of drinks then take him back to my place. We’d confirmed just a couple of hours before, but when I sent him the exact address he didn’t reply.

Texting with two girlfriends, the consensus was he was an insensitive jerk who had stood me up. It didn’t feel right, but it was odd.

A couple of hours later he texted “Ann I’m so so sorry… I fell asleep on my couch.” We spoke on the phone. 

He was sincere.

I was horny. 

It was 10 pm. I hadn’t had sex in three weeks. I asked him what he thought about still coming over. I told him it was definitely now booty call territory.

“Ummm, yeah, that’s cool… is that what you want?” He asked, clearly not used to such transparency. 

“Too transparent?” I asked.

“No, not at all. If you want me to come over, I’m all good. I will follow your lead.”

“Well, I need the stress release. Come on over.”

He was nervous as fuck. A ball of jittery energy. But he got over it enough to prove he had mad oral skills, a functioning average penis, and really, really, strong arms.

11 thoughts on “Freaking men out by my boldness, one interaction at a time.

  1. And, now, ladies and gentlemen…

    returning to the line-up after some medical and personal matters…

    won’t you please warmly welcome back…

    Number 9 in your programs, but Number 1 in your hearts…

    ANN…ST. VINCENT. St. Vincent.

  2. I’m sure you would scare (intimidate) me also! I do not have the confidence you need. It might be his problem also….

    • Thank you! It doesn’t always work… and if I think there’s relationship potential with someone I’m far more cautious. With this situation, I didn’t have much to lose. And he’d been very respectful and kind so I didn’t think I was going to be played.

  3. Ann, some guys can’t handle a strong, independent woman. I think it’s awesome, we raised our daughter and son to be assertive, don’t back down if you’re right and respect the other sex.

    • Congrats on raising assertive children. I was way too bossy when I was younger, now I like to think I know how to be a bit more balanced.
      You’re quite right that some guys don’t want a strong, independent woman. I’ve come to realize they aren’t the right ones for me either, so when they self-select out, I’m okay with it.

  4. LOL – as the Rolling Stones sing….
    No, you can’t always get what you want
    You can’t always get what you want
    You can’t always get what you want
    But if you try sometime you find
    You get what you need

What do you think?