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Awkward Moments in Dating: The Phone Call

January 6, 2019

(image via wikimedia)

Phone calls early in a potential relationship can be stressful.  During a phone call, the only communication is verbal.  If two people are next to each other saying nothing for a long time, they can still enjoy each other’s company, but that can’t happen during a phone call.  When you’re on the phone, you have to talk.

Phone calls are tough for introverts and shy people because talking for an extended time isn’t natural to us.  An introvert talking to an extrovert can work out okay because an extrovert might take charge of the conversation.  Two introverts sharing a call can be disastrous.

Jenny wasn’t shy, but I still didn’t want to answer her call (you can read more about her here).  She was cute and had great cleavage, but she still had a thing for her ex-boyfriend and had been so aggressive with me in her apartment that I was pretty sure she had issues.  Even in my twenties, I knew to stay away from women with certain issues.

Some guys would have thought I was crazy for not taking advantage of the Jenny situation.  I’m not really better than the guys who would have taken advantage. I’m not a saint.  I just think ahead.  I know short term fun with a woman with certain issues can lead to long-term problems.

Anyway, Jenny was prettier than I was handsome, and she had great cleavage.  The thing is, cleavage usually doesn’t matter to me that much, but hers was fascinating.  It probably deserves its own “Awkward Moments in Dating” episode.

I knew Jenny was going to call.  I’d told her at the end of our date that I was going to call her even though I’d been sure I wasn’t going to.  It was a douche thing to do (“Douche” was a term in the 1990s), and I prided myself on avoiding douche moves when I was dating.  But yeah, I lied to her.

When my phone rang on a Saturday afternoon (we didn’t have caller ID back then) a week after our date, I was pretty sure it was her.

“This is Jimmy,” I said.  I like to announce myself when I answer the phone.  It’s an easy assertive move, even for an introvert.

“Hey, Jimmy.  This is Jenny,” she said.  I don’t remember if those were her exact words, but I remember that I could tell she was nervous.  How could a woman like Jenny be nervous?  Normally, I’d be the nervous one.

“How are you?” I asked.

“Fine,” she said, and that was it.  I wondered how she didn’t have anything other than “fine” to say.  She was the one initiating the phone call.

“I had a good time last week,” I said, leaving out her Garth Brooks obsession, her ex-boyfriend, and the snot running out of my nose from the overly spicy food at her ex’s restaurant.   “I… um… probably should have called you this week.”

Ugh.  I probably shouldn’t have acknowledged that I was supposed to have called.

So I added, “There was a lot of stuff going on this week.”  That was a lie.

“That happens,” she said.  She knew I was lying.

The short sentences threw me off.  The Jenny I’d gone out with would have talked right over me and told me everything about her past week, whether I was interested or not.  This was like a robotic Jenny.  I didn’t know how to talk to robotic Jenny.

“So what’s going on?” I finally asked.

“I know it’s late,” she said, “but do you want to do something tonight?”

I was surprised she asked, considering what a disaster this conversation was.  Maybe her ex-boyfriend was working, I thought.

Oh man,” I said with fake exasperation.  “I already have plans.”

I wasn’t lying, but the plans were lame.  I was going to a sports bar with a bunch of friends to watch some football games.  They would have mocked me if they’d known I was turning down a date with Jenny just to hang out with them.  I made sure never to tell them about the phone call.

I didn’t even explain to Jenny what my plan for the night was.

“Maybe another night,” she said.  We both knew there would be no other night.  She actually sounded disappointed.

I was accustomed to being on the receiving end of phone call rejection.  Suddenly, I understood how all those high school girls and college women (the first couple years) had felt when they turned me down.  There was a little bit of guilt, but what else was I supposed to do?  Go out with her just because she had great cleavage?

I should have told her that I thought she still had a thing for her ex-boyfriend.  That would have explained why I was reluctant to go out with her again.  She should also have known not to take other guys to that restaurant again.  I couldn’t urge myself to tell her not to be too forward with a guy on a first date, especially if the date hadn’t gone that well.  Looking back, maybe I should have told her.

Maybe it was easier to lie because I knew I’d never see her again.  It’s easy to lie to strangers.  Sometimes I do that just because it’s more interesting than telling the truth and there’s no real consequence for it.  If a stranger catches me in a lie, who cares?  Again, this was before the internet and social media.  Back then, Jenny couldn’t get on social media and tell thousands of followers what a jerk I was.

People get mad today when a man or woman in a relationship ends it with a text.  I kind of understand delivering bad news with a text.  It’s wrong, but I understand it.  Breaking up with Jenny over the phone was really uncomfortable, and we weren’t even officially dating.


The dating saga with Jenny is over, but Awkward Moments in Dating will continue next week with a brutal tale of high school rejection (and I was on the receiving end this time)!

In the meantime, you can start Awkward Moments in Dating  from the beginning!

From → Dysfunctileaks

  1. Oh, that whole exchange just sounds awful. But I am sure you probably saved yourself a whole bunch of really disconcerting experiences by terminating the Jenny relationship. And your right, I can’t imagine what it must be like to date in the era of social media, where people announce every thought and movement they make!!

  2. Break up etiquette is such a difficult thing. I once spent a few days trying to avoid breaking up with someone via text (we kept missing each other’s calls), and then he broke up with me via text. Oh, the irony…

  3. Hahaha
    This is really good to read!

    Couldn’t help but smile

    Would love to hear your thoughts on my post! M

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