Boyfriend Roulette, Shrinking Yourself Down & Doing Your Own Thing


Men. Gah.

Women. GAH.

All the time I get asked — “Are you dating anyone right now?”  Sometimes the answer is — “Gawd no”… other times it’s “dating around”… often it’s “I can barely take care of me, why on earth do you want me taking care of anyone else?” ROAR.

I’ll meet a new friend, who happens to be of the opposite gender — and BOOM — the friends pounce. “Who’s the new guy?” “Awe, you two would be so great together” “This is PERFECT. You can bring him to our wedding this summer.” …blah blah BLAH. I usually respond back with a “We’re just friends.” — and  about 64 eye rolls. The debate then starts on whether women and men can be friends. The girls say — of course, they can! The guys — ALWAYS say, nada, no way, not in a million years, babe.


Here’s the thing… if I wanted to snap my fingers and be in “a relationship” right now… I could be. Simple as that.

It’s not hard to find a young buck, lock eyes and frolick into the sunset. Hell, people do it each and every day. You go out, meet a few guys at the bar, plan a date with one of them — and then continue on that rotation until you find one you can tolerate for a week. You both “settle” — likely because you both don’t know what you deserve, want or need. You both don’t talk about that though… you talk about everything else, planning weekends away and date nights with friends. Soon enough, you’ve been together for 3 months, 6 months, a year — and then depending on how self-aware you are, you either accept that this is what you deserve or you break if off.

I’ve been there. I’ve done that. In 2012, I vow’d to never do it again.


Lots of people date for the sake of dating (aka DSFD). They like meeting new people, like the stories that come from bad dates and end up carving out what they’re looking for. It’s social, fun and can make you feel like you’re working towards something.

I get why people do it. I really do.

When I think of DFSD, I think of boyfriend roulette. You walk into a coffee shop,  a guy looks you up and down, and you think — YEAH, BABE. He approaches you over your Grande Soy Americano Double Whip Misto Crap… asks for your number and you agree to Friday night at 7pm. Romantic. You go to dinner to find out he’s a nice guy but there’s no chemistry. You don’t want to reject him {he’s not that bad after all}, so you agree to a second date.

At the gym the next morning, you notice a new guy lifting weights. You smile at each other and continue busting your groove on the elliptical machine. When you head to the mirror to do some squats, he approaches you and starts up conversation. Soon enough you’re laughing, he’s not staring at his biceps anymore — and you agree to coffee on Sunday. You skip Sbux, hit up a local joint and lock eyes over itty bitty cups of espresso. An hour turns into two and soon enough, he says, “I’ve gotta run. I’ll call you.”

You never hear from him and he never returns the gym. You go back to coffee shop guy and meet up for date #2…

Dating for the sake of dating stresses me the hell out. It’s not the conversation, time or meeting someone new that’s the problem… it’s the meeting someone who you wouldn’t normally spend a second of energy on.

I don’t have anyone in my life that’s average. Yep, true story. The people I have in my life and the people I continue to surround myself with are anything but average. {We’re not talking physical folks, we’re talking smarts. Not saying that they’re not babes… but you know what I’m saying…} The biggest challenge I have in the dating world right now is that I feel like I have to dumb myself down to get through a date. No, I’m not a brainac, nor the most awesome chick on the planet. I’m just a girl who cares more about a 9 to 5 job, a cat and watching football on Sunday’s. Not that there is anything wrong with cats or football…


I agree to the date, actually legit look forward to it — and meet the guy. He has it all together — good job, friend circle, hobbies and doesn’t seem to be a serial killer. The problem? It feels superficial. I ask him about his job… he tells me, he’s been there awhile and it’s ok, pays the bills. I ask him about his friends and he says, that he’s had them for years and they’re the best! His hobbies include watching TV and playing hockey a couple of times a week. He sits there content and happy, without much care in the world. I try to dig deep and I get — nothing.

At that point, I have two options:

  1. Play down who I am and just give him high level — which generally means a second date.
  2. Be who I am — which generally intimidates/terrifies him and we end the night with a hug and “it was nice to meet you.”

Generally I choose the latter. How the hell are you going to meet someone amazing unless you show up and be who you are? I go into every date with the best case situation of making a new friend. More than that? Not even on my radar.

When  they ask me what I do for work… I tell them — with passion, excitement and energy. When they ask me what I do outside of work…. I tell them — giving back to the community, working with youth and travelling the world. I babble on asking them about their life, telling them about mine and eventually he says:

I’ve never met a girl like you. Awe. A sweet nothing. UGH.

There is a huge difference between… I’ve never met a girl like you {and there is no way on earth I’m ready for it} and I’ve never met a girl like you {and I’m stoked for the challenge}. The illusion of dating women like me is intriguing. I get that. But you know what? It’s also tough as hell. Dating a woman like me means you are going to have someone who asks you to be vulnerable and authentic — all while encouraging you to dream big, follow your heart and be the best version of yourself. And in today’s world, lots of people aren’t ready for that.

I believe that the thing that makes me different from let’s say — “average,” is that I am assertive and self-aware. Dropping truth bombs like it’s hot. The part I struggle with about “I’ve never met a girl like you” is that if you truly believe in surrounding yourself with people who lift you higher… then you should have friends like me. Right? <Insert Silence>.

Recently on a date, I asked a guy: “What excites you?” {… thinking it was a basic question.} He paused and responded with: “That’s a hard question. I’ll have to think about that and get back to you.” I sat there… stunned.

To be honest, he could have said anything. The answer itself didn’t matter. What mattered was that he cared about something that was bigger than himself.

I’ve dated people who don’t get me. I’ve dated people who’ve pretended to get me. I’ve pushed every ounce of me aside in a relationship to give to a significant other. In every single one of my past relationships, I’ve dumbed myself down. EVERY SINGLE ONE.

I recently read a post by Danielle La Porte that hit the heart. Within it, she wrote:

“The next opportunity to meet, to work, to dine, to interact, to kiss, to speak, to spend, to serve (no matter how shiny, sexy, lucrative, coveted, necessary, obligatory or useful it may seem), ask yourself this:

Will I have to shrink to make this work? or Is this a place where I can expand?” 

Simple, profound and something we all need to keep top of mind. In order to be your best self, you need to surround yourself with people who will help you shine.


Settling scares the shit out of me. 

I don’t want to ever meet someone who thinks — damn I thought I could do better than Jillian, but hey, this is better than nothing. Does that give you hives? I think I’m already breaking out.

According to some random article that I recently read, the #1 thing that people settle on is personality. PERSONALITY. Good gawd. I’ve been there, yes I have… and I don’t wish it upon anyone.

I think we’re  all realistic enough to know that a lot of people are on the search for perfection {terrifying}. When they can’t find what they’re looking for, they settle. All of those people need a little wake up call on real life. Oh hey, you’re not perfect, your significant other won’t be perfect and NO ONE is perfect. A cat, a dog, 2.5 children, bills that pay themselves and a white picket fence? That’s imaginary land!

Deep dive into your relationship. If the bad outweighs the good, you owe it to yourself to get out and move on.

Get to the root of what’s motivating you to settle. Lonely? Fear of being single? Frustration with years of dating? The ticking time bomb in your ovaries? For years, I settled because I believed I didn’t deserve any better. Awful, eh. If there’s any ounce of learning that comes from this post, I hope it’s the following:

If you don’t value yourself, you can’t expect anyone else to value you either.

Once you’ve thought through why you’ve been settling, then figure out your deal breakers. Smoking and drug use are obviously turn off’s, but I’m also an absolute no go if someone isn’t passionate about something. Whether it be your love for running, writing, science or the arts — you gotta be living for something.

What are those those things that you must see in your significant other or must have in a relationship? For me, it comes down to values. Respect, communication and support are huge for me. If I trust you, I tell you everything. I give more than I take — and friendship means the world to me.


Here’s the thing about getting older… you start to figure out what you want. Yeehaw.

When I was a young bird, I mostly dated the bad boy aka the jerk. They were charismatic, a shit ton of trouble and the worst communicators {no offense meant guys, I’m sure you’re good guys now}. I would clamor for attention. They would get drunk, not come home, sometimes cheat and keep me around for fun.

Eventually I grew up and learned that I deserved better than that. I went from dating bad boys to meeting good guys. My immediate reaction was — “wow, he’s boring.” Seriously. The thing about bad boys is… they’re challenging — and a little part of them is intriguing. You think you can change them. Part of you thinks that their disrespectful behaviour is normal. All of it is a bit of a effed up bad news bears vortex.

Slowly I learned that just because a guy is a nice, lovely and treats you well, doesn’t mean he’s boring at all. In fact, nice guys and nice girls generally make healthy relationships. Surprise surprise! Honesty, trust, empathy, respect, shared values — all seems pretty good to me.

When I think about what I want in a relationship, first and foremost, it’s emotional connection. I need to ‘get’ the other person and they need to ‘get’ me. I believe relationships hit all new levels when there is compassion, laughter, an understanding that it’s ok to make mistakes {and learn from them} and a mutual desire to grow, both individually and as a duo.

I know that’s out there and one day when I’m ready, it will find me. Someone will walk into my life, look into my soul and see me for me — crushing my fears, embracing my dreams and loving perfectly, flawed me.

It won’t be perfect. It wont always be easy. But 100% it will be worth it.


The most lonely you will ever feel is when you realize that you’re in a relationship that’s not right for you.

Be happy with yourself before you try to find happiness with someone else.

If you want to date someone great. Be someone great.

// end rant


  1. Pete Williams (@preneur) January 5, 2014

    The best dating advice I ever heard was:
    “Figure out what your ideal partner wants in an ideal partner … and work on becoming that”

  2. Loved this, Jillian. <3

  3. Jeremy Lim (@jeremylim) January 5, 2014

    Such awesome advice! I love proactive perspectives on dating.

  4. Michelle January 5, 2014

    I love, love, love this. And you. xo

  5. Cecilia January 7, 2014

    You’re smart – don’t waste your time with the wrong person, all of us deserve so much better!
    I took it as far as being married before I realized that he was the wrong person for me. It wasn’t easy, but I ended it after 8 months althoug he is a great person he wasn’t the one for me…

  6. Meghan January 9, 2014

    It frightens me how many of your comments about past relationships mirror my own experiences. Great post, I really like your perspective.

  7. Mike G January 27, 2014

    Maybe your looking in the wrong place. Quality men sometimes are hidden as Hooter’s girls :-)

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