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Emily Straubel

Emily is a sex and dating crusader. She founded The Red Lipstick Project as a place to talk openly about dating and sex and to connect with other intelligent women who want to find relationships that are as passionate and ambitious as they are. Emily also works with these women as a certified Holistic Health Coach to focus on their health and mindfulness as they go through breakups, job changes and other transitions to feel and look amazing in their own unique bodies. To share your story or experiences with dating in Portland email her at

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The Sex Files with Emily Straubel
Posted: February 17, 2014

3 harsh truths you need to get over when dating in Portland

Last week I was on a steamy date with a super sweet guy. We were snuggled in at the bar of a crowded restaurant and halfway through a heated discussion about the quality of the post-trilogy Indiana Jones mini series “The Young Indiana Jones” when a cute couple walked by. Both he and she gave me a high-five as they sat down at a nearby table. My date, who is “from away,” was mystified to hear that the guy was a recent ex-boyfriend of mine and the girl was the one he dated directly after me. This seemed to bring out a flood of inner fears and insecurities about dating in a small city, and these feelings are legitimate, but worth getting past.

As anyone who has lived in a large city before moving to Portland knows, there is an anonymity to dating that allows you to go on dozens of first dates in a week, date more than one person at a time, or abruptly end a relationship. In NYC, San Fran, or LA  you can easily hide behind knowing that a questionable first date with a cougar you met on PlentyofFish will never be seen by friends, and you can completely avoid an ex simply by moving to a new neighborhood or keeping a wide berth from their fave locales. Here in Portland, those are not luxuries we have.

And honestly, thank God! I have (after many years of complaining about these things) learned to embrace the quirks of dating in the awkwardness that is our little city.

There are three harsh realities that keep many people from fully committing to dating in Maine. And they are facts people cling to like life preservers as excuses for being alone forever. (womp womp) But there is hope, and it comes in the form of tough love.


1. Your new love interest has dated someone you know

Unless your new lover has been celibate or they just moved here from Brooklyn (you lucky SOB) they have almost certainly dated someone you know, you know OF, your friends know, or your ex knows. And all of these notions are quietly disturbing in their own way, if you let those thoughts fester.

Don’t. Don’t let the thought of them with someone else get in the way of you being with someone amazing. If you’ve ever said “He’s great, but he and my ex were in the same dodgeball league…” you are screwed. Everyone knows everyone and we need to get over it.

Acknowledge it, acknowledge how weird it is, and move on. Although books that list dating “rules” tell you NEVER to talk about an ex on a first date, if you know each other’s exes, that advice doesn’t work here. Get it out into the open and break down the awkwardness that will inevitably explode if you pretend like you don’t know that he dated the same Kate who serves you your morning (and afternoon and late afternoon) mocha. It’s going to be weird and awkward, but hey, what isn’t on a first date?

There is nothing more attractive than a person who isn’t paralyzed by jealousy. Except maybe Indiana Jones.


2. Online dating is ubiquitous and deeply flawed

I can’t tell you how often I hear people say that they’re afraid of online dating or posting a photo to their profile because they are embarrassed that people will see them and know they are single. Really? And you wonder why you’re alone forever? Because no one knows that YOU’RE SINGLE!

God forbid the smokin’ hot guy who works down the hall from you finds out that you are also on the market (he is likely single if he sees you on OkCupid… duh) Then he might actually ask you on a date! That would be horrible!

If people know you are single, they are more likely to ask you out, or hook you up with a friend.

And there is nothing to be ashamed about. Everyone’s dating online. This isn’t the 90s and online dating isn’t porn (Tinder excluded). Get over the stigma and put yourself out there. If you have ever wondered how that nerdy girl landed that super cool boyfriend, she took a chance and messaged him on OkCupid. It could have been you, but you were waiting for him to message you. As an online dating guru, I can tell you that actually never works out.

That being said, if you’ve been online for a few weeks and haven’t found your soulmate, don’t stop. Online dating is deeply flawed. I’ll get into this in future episodes of THE SEX FILES (cue mysterious opening music). It’s flawed, but it’s not futile. I have met amazing friends and lovers and boyfriends online. In Portland.

There is hope people. Keep up the good fight.


3. Make outs and breakups are highly visible

This truth is a tougher pill to swallow because there are so many emotions involved. A make out sesh on the dance floor while jamming to Clash of the Titans at Empire feels so right. But if you’re recently out of a relationship, there is a good chance that the news of your drunken tongue-lock will make it back to your ex like a middle school game of telephone. And this is one of those truths that can cause real-life heartbreak. And I would never say don’t go for it (whatever IT is), because those spontaneous moments at the beginning of a relationship are so special. But know that you’re sharing it with a small community of sometimes judgmental people. Choose your actions accordingly.

Also, be a part of the solution, not the problem.

Don’t judge people before you know the whole story. Often rumors fly about people during their most vulnerable moments, primarily breakups. If a new prospective date is known for a highly visible argument or bad behavior during a tough breakup, give them the benefit of the doubt. Get to know them before writing off their actions as part of their character. We’ve all done things during a breakup that range from insane to slightly out of character. Get to know a person and cautiously be aware that they may in fact be insane.

Are there other universal truths about dating in a small city that you think people need to just get over? 

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