Dating Red Flags: Being Asked Out via MSN

After my first ‘relationship,’ if it can even be called that, you would have thought I knew better. Yesterday, I posted a poem I wrote in 2004 where I realized I could not shoulder the world’s burdens. That girl must have taken a time out in 2006. My 16-year-old self relapsed into thinking she could carry the weight of the world on her shoulders. It was that way of thinking that would lead me through three months of red flags.

This is just too much for one blog post. I’m calling this the *Zachery Saga.


High school is fulled of crazed children with even crazier hormones. I didn’t care for any of the drama I saw so many people get involved in, but I was always willing to offer my opinion if it was requested, especially for my best friend. She was in a bind between two brothers, one a year older than us and one a year younger. They both expressed interest in dating her and she was trying to make a choice.

These brothers were like night and day. The younger was a lively goofball with an annoying habit of pushing people’s button. The older was introverted and quiet. He hung around our group of friends, but rarely engaged. To an onlooker, it would have seemed like he was eavesdropping on us because he never really stood with our group either.

She choose the younger brother.

Some awkwardness followed because the older brother, the one and only Zachery, felt like my friend had been stolen from him. Eventually, things seemed to settle into a normal rhythm. That would be my mistake.

Not longer after my friend’s relationship began, I was talking with her over MSN. It was late and we were both getting ready for bed. The moment my friend logged off the instant messaging service, I had a message from Zachery.

If only they looked like these brothers, the relationship would have still been a bad idea.                 This photo, “Paul Wesley & Ian Somerhalder” is copyright (c) 2014 vagueonthehow and made available under an Attribution 2.0 Generic license

He asked, via MSN, if I was interested in dating him. In hindsight, that was a big red flag. He couldn’t even ask for my phone number is use his voice to ask me out? It didn’t matter, because I didn’t really have the self-esteem to say no.

I wish my friend hadn’t logged off. All I wanted to do in that moment was ask for her opinion. He probably asked me out at that moment because I couldn’t lean on my friend for support. I was alone in this internet space, without a trusted companion from whom I could seek counsel. I accepted his offer after noting that I wanted to take things slowly.

 My relationship with Zachery would spiral real fast. He was both clingy and quick to anger. More than once during our relationship, I would fear for my well-being or the well-being of those around me.

I think about this moment, when he chose a computer as his method of asking me out, as a sign of bad things to come. He picked that method because it was easy and I would soon learn he took the easy way out when possible. He’d even speed up his car so he didn’t have to be bothered pressing his foot to the pedal for too long.

I still wonder if he picked me for that same reason. Did he think I was easy? Maybe he was just looking for an excuse to get close to my friend, even though she was dating his brother.

What is the worst way you’ve ever been asked out? Did you accept? Looking back, what sort of red flags do you see in your failed relationships? Would you ever date a family member of your friend’s significant other?

Stay tuned for next week, when Zachery drops a four letter word and I realize just what I’ve signed up for.

*Zachery isn’t this guy’s real name.


37 thoughts on “Dating Red Flags: Being Asked Out via MSN”

  1. It may be weird but I usually went for a cup of coffee getting to know the person who we was chatting with. and ended up in bed LOL
    And no never date a family member unless you want the other. yeah I know it is crazy but the only reason people do. If you ask me

    We all learn, one mistake at a time. I had my fair share.but hold no regrets.

    1. Coffee is a pretty good start as far as I’m concerned. I think coffee dates are perfect. If you don’t connect, you can easily make an excuse to be busy and leave. If you connect, you can suggest to grab lunch or dinner after the date and extend the experience. I suppose that could easily extend into the bedroom ^_^

      I definitely wrote a piece on coffee shops being the perfect dating spot back in my days as a ‘dating expert.’

    No, but in all seriousness, this guy seemed like a creep in the beginning, but it seems like you didn’t know much better. Hell, my previous dating life is a series of “spaghetti moments” (based on the meme that something is so awkward the spaghetti falls out of your pockets).
    But anyways, I’m interested in seeing how this unfolds.

    1. Dude, I think tossing me a note when I’m not looking is adorable. At the very least you had to take the time to write the note and approach me. I once saw a story about how this guy asked a girl out at a coffee shop. She was sitting reading a book and when she looked up, there was a note on her table. The guy introduced himself in the note, saying something about how she looked too cute reading her book to be disturbed. The only thing left was his phone number. I’d circle yes on that one.

      You don’t even know the half of it. Our relationship only lasted three months, but I have plenty of stories to tell (which will all be told here ^_^)

    1. Here’s the funny thing, he didn’t even ask me out on a date. He just asked me out. The next day, we were boyfriend and girlfriend. We didn’t go to a restaurant to hang out and see if we wanted to date or anything. We just were. At 16, going on a real date shouldn’t have been that hard. I wasn’t thinking clearly at all.

      1. Well, I was thinking clearly after our first date when she showed me a poem that she had written for me…

  3. When I was on Plenty of Fish, the online dating site, for not even a week, a guy asked me out to Apple Bee’s. Maybe that doesn’t sound ridiculous, but there are so many amazing places (not necessarily expensive) to eat in my area, and the best thing he could come up with was Apple Bee’s. I thought it was funny. But the worst way I’ve been “asked out” was in elementary school when girls bullied me by getting a note passed to me from a guy that asked me out. Well, it wasn’t really from that guy…it was people picking on me. Thankfully I didn’t let it affect me too much.

    1. Like I told eskopoet, Zachery didn’t even ask me on a date… he just asked me out in general. The next day we were boyfriend and girlfriend. Certainly at 16 more could have been done. I should have had higher standards.

      I got made fun of in that fashion too, except the boys in question were in on it too. They would surround me while the one asked me out and everyone else snickered…. getting way too close in the process. it got bad enough, my parents thought about going to the principal using the words “sexual harassment,” but I begged them not to. The guy was best friends with, and would eventually date, the principal’s daughter. The cards were stacked against me from the start. Oh well…

  4. Being asked out via text message from out of the blue in the most dismissive “so you want to have dinner with me or not” way possible. Yeah that one didn’t work out for long, then again I usually just ask if she would like to go get coffee with me as a starter. I know I’m not the most imaginative when it comes to that first date thing, but I always preferred talking before anything else. All in all, I’m happy to have quit dating a while back I feel better without it most days.

    1. At least a text message requires effort. You have to get the person’s number somehow. Creativity isn’t super important, but some kind of effort should be put into it.

  5. i think that was the trend back then. I was asked out via AIM in middle school. I ended up dating the guy for almost 2 years. He was 100% gay at the time (but in hiding) and is now my gay best friend. I can’t say that relationship was bad. He treated me very very very well and always thought of me. we spent a whole lot of time together and had fun and really became best friends (which is why when we broke up we remained friends). We always make this joke that he treated me like a queen because he was a queen. lol but anyway, I don’t think the mode in which they ask you out is as important as who the person is. I mean I got to know my gay bestie for months before he asked me out, chatting constantly on aim and hanging out at school so I had an idea of who he was. So when he asked me I was delighted and knew what I was getting into (But obviously didn’t know everything I was getting into since I was the last person on earth to even think he was gay and no joke when he came out shortly after we broke up everyone told me they had a feeling or thought he might be. Never crossed my mind. lol). Anyway, I don’t know if this was the case for you and you had a grasp on who he was but when you started dating he flipped, or if just out of the blue he asked you out without even knowing you first and you had to make a hasty decision. But as I’m sure everyone knows, our judgement isn’t always the best in adolescence either. Live and learn right.

    1. He just asked me out of the blue. I don’t even know why I had him on MSN. I probably got a notification he added me and just accepted because I knew he existed. He never said anything though. He was always on the edge of our group and never engaged in order to build any sort of friendship. It was my mistake thinking that would change once we adopted the labels of boyfriend and girlfriend.

  6. Zachary doesn’t sound like much of a prize. Your reference to him being rather lazy made me think of the old joke about the guy who married a girl who was already pregnant because he was too lazy to do it himself. I look forward to finding out how things worked out. I’m guessing that you’re NOT Mrs. Zachary!

    On the other hand. I met my husband online. As an elementary teacher. I didn’t have many men to chose from above the age of 8, so online dating was a good option for me. 14 years later, our marriage is happily going strong! 🙂

    1. No, I am definitely not Mrs. Zachery, although that friend did end up marrying his younger brother.

      I don’t see a problem with meeting online. I assume you got to know each other a bit and then went somewhere on a date? That’s normal. Saying “hey, be my girlfriend” to a girl you hardly talk to is a bit abrupt. I should have insisted on a real date before I agreed.

  7. I am in middle school and i have not had moments like this with “Mr.Lazy Guy” because i am a male though i have tried asking girls out with little notes with checkmarks “yes” or “no” sometimes works sometimes don’t though if you want a real relationship this video shows you exactly how sorry i do stuff like this..

    1. I think notes are cute. That’s something you do in person and, if the relationship works out, that piece of paper may turn into a precious memory. Poems are cute but, even though I wrote poems, I was rarely impressed by them. Apparently, I had higher standards for creative writing then I did for people. My 16-year-old self had so much to learn.

    1. I have never seen that movie. This guy could use a lot of work, but I can’t fault him too much. He was only a teenager, after all.

  8. So I guess this was the antecedent to relationships via social media and texting? I agree that it’s a poor substitute for calling and face-to-face communication. It’s too easy for more cowardly moves. I was stalked and sexually harassed by a young woman via of LiveJournal and a UNIX talker… Cimmorene was hurt but she helped me put a stop to it.

    1. You know what bugs me most about it isn’t even MSN. It’s that he made a point to cornering me seconds after my last friend got off line. I had no one to ask ‘is this a good decision.’ I should have told him maybe and made a decision after talking to someone.

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