You’re Intimidating. That’s Why Men Don’t Approach You

A Brief History of Dating


Let’s talk about dating. I am not a woman who has done a whole lot of dating in my life. I was always “one of the boys” in high-school and a young woman with my aesthetic, back then was not a commodity like it is now. I lived in a city where the beauty standard was thin white girls — no shade, just facts.


There are a bunch of reasons for my lack of dating experience post-high school. The top rated: A decade of school made me serious about my studies; I moved to two new Provinces, knew nobody and had to make new friends; I wasn’t really open to dating; men rarely approached me; I lack subtlety (I’ll get to this later). 


What’s the Problem?


The most common thing I’ve heard (men and women alike) is:


“You’re intimidating, that’s why men don’t approach you”.


This makes me want to bang my head against a wall.  It chips away at my soul. I am not a sensitive person and I don’t generally take things personally, but this irks me on a visceral level.


The definition of “intimidate” (you’re welcome) is:




  1. frighten or overawe (someone), especially in order to make them do what one wants.

Let me tell you. I do not frighten men into going on dates with me (I’m actually laughing out loud typing that hahaha). If you know me, you already know that I’m probably one of the friendliest people you’ll ever meet — no joke.


This has been a topic of conversation with a good friend of mine for sometime. He insists that men are intimidated by me and would argue that I’m misinterpreting the definition of “intimidating”, making it a bad thing (umm please see definition above sir). He thinks that men get a “vibe” from me, and this coupled with my attractiveness (his words not mine), makes they’re less inclined to approach me. They think I’m “out of their league” and “unapproachable”.


I take issue with this on so many levels.


How in the name of Yeezus am I supposed to control other people’s assumptions? The word “intimidate” is a verb, i.e., an action word — meaning that I would  need to be doing something for this to be true. If I am standing around, minding my business and someone assumes that I am a certain kind of way, how can I change that?


The interesting thing here is that over the last year, since I’ve been having this conversation, I have definitely been approached by more men. Don’t get it twisted though, when I say “approached”, I mean +/- 10 strangers slid in my DM’s on Instagram and commented on my body. I’ve also gone on two dates — this sounds promising, but I’ve lived in Toronto for almost 4 years. Not a good ratio.


I’ve wracked my brain over this for months…. Legit. I think what people (my friend included) are trying to say is that I am a woman who has presence — a lot of it. Presence is something that may make people feel a certain way about approaching me. Especially men. But let’s keep it one hundo: Having  presence and being intimidating  ≠ the same thing.


I’m an introspective person, so I can’t put all the responsibility on men for my dating struggles. The other BIG problem is that I lack subtlety and this is 10000% a me problem. I am really really bad at flirting and reading subtle cues for things. I’m just oblivious.


I’m that woman who will  ask if I am not sure. One time a guy sort of  asked me on a date, but there was no real question put to me. So I said, “Are you asking me out on a date? I’m unclear about this.” I needed to be clear.


I was taught never to assume anything. My parents said “Cleo, if you want to know something – ask because you’re not a mind reader.” (Unlike my late-night name twin, Miss Cleo the psychic). I NEVER assume that a man who tells me I’m attractive or is nice to me is trying to get into my pants. I’m not a bleeding narcissist.


By not assuming, I often miss the subtle cues that come with flirting. School me please! I am an excellent student.  It’s not in my nature to be flirtatious. Anything beyond being my usual self feels forced and ridiculous.


What’s the Solution?


As a solutions oriented person, I asked people how I can fix this. I’ve researched tangible strategies to implement to no avail. I already do all the “tips and tricks”. I smile when I meet new people. I laugh easily. I am polite. I maintain eye contact. I shake hands. I talk — What else I’m supposed to do here?


Here are some of the trash suggestions the interwebs has provided about how to flirt:

  • Touch his arm”… WTF I touch everyone I meet are you kidding me? I have no qualms with physical touch, and to make people comfortable, I often touch their arm when speaking with them. How in the f*ck is touching someone’s arm flirting?
  • Smile when speaking to him”: Again, I smile when I speak to most people. I am not a shy woman, so can someone get more specific here for me?
  • Play with your hair”: Stop this right now. Have you seen my hair?
  • Be Expressive”: Have you met me? Go watch one IG video of mine and then take your seat, internet.
  • Be Girly”: …………………SRSLY SRSLY??


So, that was wildly unhelpful, thanks for nothing internet.


I’ve also tried online dating a couple of times… and kids, let me tell you, it’s hard out here in the online streets. I keep receipts (always), and here are a few gems:

This video is awesome too…and if you’re not crying laughing after watching that, you need Jesus.


Online dating is a struggle for me because I like to build rapport with people. And I prefer  to do that face to face — definitely not through unsolicited d*ck pics or telling me you want to “eye blind” me and put me in a tub.




Since the internet is useless, the solution seems to be to just continue being myself. I refuse to dim my shine to make someone else feel more comfortable/confident — I am who I am and I like her.


That said, closed mouths don’t get fed. So if I’m going to start dating I need to do a few things:

  1. GO OUT CLEO: I’m admittedly a bit of a recluse at times because I’m an ambivert and I really enjoy spending time alone. I go out lots for work events, but when given the choice between a book at home and a party, I’ll probably choose the book and my bed.
  2. Woman Up: If men are afraid to approach me, then maybe I need to approach them. This should be easy, I make friends with everyone right?
  3. Just Ask:  I think sticking with my usual MO and continuing to be direct is the way to go. But maybe I’ll take the initiative and ask him out rather than waiting for him to ask me.


Chime in friends. I would LOVE to hear your opinions. Maybe I’ll make it a whole dating series?  I’ll test my theories this summer and write about it. Let me know in the comments if you want me to give this a whirl.


Until we meet again my loves,




For You

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