Kate Bergstrom is Dates With Kate. She runs a web site (featured on the front page of the Seattle PI), a podcast and authored a book. She has gone on over 100 dates over four years in search of – what? She has gone into the world of online dating, that’s clear. She is bold, open and funny. In a way, she does this experimenting for us, her readers and listeners. The Monarch had the chance to chat with Kate about her past three years: 

Jake Uitti: You’ve said you’ve gone on over 100 dates with men you’ve met on the internet over the past four years … how did this start? And what’s the worst date you can remember?

Kate Bergstrom: I was in a long relationship (almost 6 years) and, when it ended, people were just starting to talk about online dating, so I decided to check it out. It was a fairly new concept but I just jumped right in. I started the blog/website because I had several friends that were living vicariously through me so I thought I should put the stories on the internet and see if other people were going through the same things. Turns out they were!

The worst date? That is hard to narrow down. I have been put in a headlock, had a guy (with no notice or encouragement from me) totally disrobe while I used the bathroom, watched in horror as a guy drank six drinks in 30 minutes and warned me to watch for demons – the list is long. But the worst was probably a guy that totally lied about everything – his hometown, his job, his height – and he stared at me the whole time with crazy eyes. I am not sure he blinked. He asked me out again and, when I politely declined, he wrote me an email with the top 8 things that were wrong with me. I took a break from online dating for awhile after that guy.

JU: I remember you telling me you could have a drink with anyone – that staying on a bad date with someone for at least a drink was doable. Do you still believe this?

KB: I totally still do. I think if you can’t do at least that – if it is too terrifying or you are afraid of wasting your time – that online dating might not be for you. Most of the time you have to meet a few people before you click with someone. I think one of the best things that online dating has done is given me the ability to have a conversation with anyone. When I first started I felt like I wanted to puke I was so nervous and now I get almost excited to talk and learn about someone new. That attitude shift is what I think keeps daters sane.

JU: You’ve become so well versed on the topic of online dating that you’re putting out a book! What part of the book are you most excited about?

KB: Yes! I am still pinching myself. Seeing your own name on the cover of a book is pretty excellent. I think the thing that I am most excited about is that I get to really go into depth on my tips for daters, both for those new to it and for people that have been doing it for awhile. On my site and podcast, I tell the stories of my dates but I don’t really get to explain in detail the lessons that I have learned. I really hope that people can learn from my mistakes and experiences so that they can maybe spare themselves similar pain!

JU: What’s the tip you wish you were told before going into this dating thing?

KB: I wish that someone had told me to be prepared to meet guys in all different stages of emotional availability. I think online dating draws all kinds of people, in all different stages. I have been on dates where the guy wanted to get married as soon as possible, I had one guy cry because he felt awful that he wasn’t giving his wife and family another chance and one fine fellow that was still living with, and sleeping in the same bed (!!!) as his soon-to-be ex-wife.

Related to that, I learned that I want guys that are officially divorced and not just separated. I dated a guy on-and-off for over a year, waiting for him to get divorced, so that he could actually be my boyfriend and not a guy still married to someone else. I think that if I would have met him when his marriage was actually over that our relationship would have had a much better chance. Separation is just messy business.

JU: What is your hope – what do you want – from all of these experiences? To see a vast array of evenings? Is it for a more singular goal of marriage? Do you think your book, web site, podcast can speak to a wide variety of women with a wide variety of interests?

KB: For me, I would totally be willing to get off of the dating roller coaster. It is fun but it is exhausting and ultimately, I would love to settle down with one guy! I have painted myself in a little it of a corner by being an ‘expert’ on dating – I would have hesitation about dating me, too – but I am not giving up. I think there is still a guy out there for me and I am going to have fun trying to find him.

And, yes, I think my advice – in the book, on the podcast, on the blog – is basic enough that it can apply to all types of women and men. I have started having guest posts on my site (including you, Jake!) and I have some guests coming up on my podcast so that my voice isn’t the only one that my fans hear. People have all kinds of experiences in the love game and I think the more that are shared the better.

JU: Do you ever wake up in the middle of the night and think, What the hell am I doing???

KB: Yes, yes and yes! If you would have told me five years ago that I would be writing a book on online dating I would have called you a total liar! Sometimes I wonder who the hell I am to be giving advice to anyone – there are lots of people that do online dating, some are more successful, i.e. getting married to someone that they met online – but somehow it is working and people seem to want to hear what I have to say – for now! I love talking to and meeting new people so it is all kinds of awesome how this all turned out. I am going to enjoy it while it lasts.

JU: How should a guy plan a (first) date, in your opinion?

KB: My advice for the first date is to always keep it simple. Agree to meet somewhere for a drink or cup of coffee so that, if it is a total shit show, you can get out of there after one drink. If, however, it is going well, you can always stay longer. For the first date I don’t think you need to overthink it more than that.

For dates after the first, I think a guy (or a girl) can do a little more planning. You already know that you kind of like each other so there isn’t that fear of being stuck with someone for hours on end. Going out for a nice dinner, to a soccer, baseball or football game, playing miniature golf – anything that gives you time to talk to each other is good. Movies are a horrible choice, in my opinion, early on. You want time to talk to each other.

JU: Got any dates coming up?

KB: For the past few months the only thing I have been able to focus on is getting my book done and ready to go. That has been my steady relationship but it is only exciting in some ways. Now that it is all done, I am ready to get back at it! I have a couple of interesting prospects and, who knows? Maybe I will go back online. I still maintain that it is one of the best ways to meet people so it will definitely be one of the weapons in my dating arsenal!