Meet Jen Kirsch: Toronto-based relationship expert, television personality, columnist and blogger extraordinaire. Essentially, a real life Carrie Bradshaw, minus the pink tutu…on the day I met her, anyway. Jen and I chatted recently about puffed sleeve sequin dresses, Jonah Hill and what she thinks you should wear on a date (not the aforementioned puffed sleeve sequin dress). She even offered me her counseling services – off the record, of course. Read on for highlights from our not-so-secret rendezvous:

The Backseat Stylers: What’s the best part of your job?

Jen Kirsch: It’s two-fold. I love the idea of helping people, especially when they’re getting out of tough situations, but it’s also kind of fun to hear all the juicy details. I’d be lying if I said it wasn’t. My job is [also] constantly keeping me on my toes. I do individual sessions, couple sessions, and on top of that I do my column, TV appearances [and] radio appearances.

What is one of the more challenging aspects of being a relationship expert?

I’ve learned that some men are intimidated dating an expert who shares some tales. Even though some are flattered, I’ve made sure to be cautious about generalizing what I write about. I value authenticity…and wouldn’t want the person I date not to act [like] themselves because they…think I might share intimate stories.

Have you ever not taken your own advice?

Absolutely! [Earlier] this year, I was dating [someone and] I sent some under-the-influence text messages that I really regretted. I was so embarrassed the next day. I ended up pitching a segment to CityTV. It took me going through it…to realize a lot of us [drink and text], and everyone needs to know [not to]!

What’s your earliest fashion memory?

My earliest fashion memory is my sister’s Bat Mitzvah. I was the baby of the family [still am] and my mom wanted me to be the princess of the ball. I was maybe 2 or 3 years old, and I got this huge poofy dress. There was some pink and there were a lot of sequins. It was back in the 80s, so just imagine really big puffy sleeves.

How would you describe your style now?

Since [that Bat Mitzvah], I’ve had very girly taste. I’m kind of over-the-top; I always try to make a statement. I haven’t worn jeans in over a year. I find that the crazier I dress, the more creative I am. On the days that I put these weirdo outfits together, I feel more confident and I put more energy into my writing. For me, getting dressed isn’t about how I look, but how I feel.

What do you wear on dates?

I’m not going to wear what you “should” wear – [a basic, you-can't-go-wrong little black dress]. I’m going to wear something awkward or different, or a flower in my hair. A woman is her best self when she’s the most confident, so she should be wearing items that she feels comfortable in and not what she thinks other people will want her to be wearing.

Where are your favourite places to shop?

I have a little thing for J.Crew. I love DVF; I think [her designs] are very loose and flirty. Lately, I’ve [also] caught myself putting things together that I inherited from my late grandmother.

If you were throwing a fashionable dance party, who would your three guests of honour be?

[Actors] Jonah Hill, Paul Rudd [and] Jason Segel. I think they would be so much fun at a dance party. I can imagine Jonah Hill throwing me over his shoulders and us just jamming out and having a good time. I’m all about sense of humour and laughter.

What are your guiltiest pleasures?

Cheese plates. I also have this crazy thing for beards.

xx, S