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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: March 17, 2014

Don't be someone's worst first date story photo

Last week I found myself traveling down the black hole commonly known as “YouTube,” and ended up watching this video more than a few times:

There is something really incredible about laughing hysterically at other people’s WORST first date experiences. Not the slightly disappointing ones where they “had a really nice time” and never texted you back. I’m talking about the epic, embarrassing, never-mention-this-happened, ever. Ironically, those are the date stories you end up telling over and over again. (In February, some of you told us your best worst date stories. And they were amazing.)

But I had a rush of nervousness after watching this…Have I ever been someone’s worst first date? Probably.

Here are a few of the things that I’ve learned from my worst date experiences. Take notes people! Let’s start giving our potential lovahs their BEST dates ever. Frankly, you can do better than this.

Dress for the day of the week

So you have a date on a Thursday night. What would you normally wear on a Thursday night? Wear that.

I see this mistake happen over and over and it really does make a difference. What we wear says something about who we are and, more importantly, it affects how we feel. I tell my clients to err on the side of casual/comfortable. I personally prefer to live by different rules since I have a thing for men in suits.  I’m working through that issue with a very well-dressed therapist. What I’m really trying to say is this: Girls, if you don’t usually wear heels, don’t start now. Nothing ruins a date like being massively uncomfortable. And dudes, we prefer chivalry over formality. Untuck your shirt and let go a little.

Show up on time

If you want to get your nerves amped up to 11 before a first date, showing up ten minutes early will give you just enough time to do that. On the other hand, showing up 20 minutes late could mean your potential lover is already feeling insecure and has accidentally chugged a glass of wine because the waitstaff is staring at them with “pity eyes.” Also, in my opinion, there is nothing more boring and obnoxious on a first date than spending the first half hour listening to your date apologize for being late and describing the traffic patterns. Worst conversation ever.

It should be noted, this rule is only for first dates (and other important dates like birthdays), and it’s just common courtesy. After that, no judgements for being late.

Turn Your Phone Off

For the love of god – put your phone away. You know what? Don’t bring it at all. If your phone is on the table and it rings or buzzes, you will be distracted. It’s not your fault, those phones have turned us all into Pavlovian robots, and you won’t be able to help yourself. But that doesn’t make it any less hurtful to the flow of conversation. First date conversation is like a sweet D’Angelo song playing on your Pandora station. If you’ve ever been jamming to a song that was cutoff by your ringtone right just before it reaches the bridge, you know what I’m talking about. Ruins the mood. You won’t be able to remember what you were talking about and will have to go into a long rant about how your mom might call because your family cat just got back from the vet and might need to be checked on. I’m asleep already.

Shoot for a 1:1 conversation ratio

Recently, my friend shared a study with me that proved, after a conversation, the person who talked more in the conversation felt better about the outcome, but the person who didn’t get as much talk time often felt less secure about the outcome (yes, I took the hint). If you really like someone, let them talk, and be an engaged and interested partner. Don’t just fire off questions based on their Facebook updates, but ask about their life and share stories of your own. Then flip the story around and ask them some questions. It’s fun, it’s called “having a good time.”

Don’t talk about sex

It’s not that conversations about sex are rude or inappropriate. Sex is something we all have in common and I talk about it almost constantly (after my first date). But many of the men I date know me as a sex writer at Red Lipstick Project, and if they’ve read my articles they know about what my turn-ons are, what kind of sex I like, and that I watch The X Files at least once a week. This is something they feel like they need to bring up on a first date. They remind me that they are also big fans of HJ’s and use words like “intercourse” and “consummate” to prove that they are sexually savvy. That is an immediate turn off, and uber-creepy. I was shocked when I learned my non-sex-writer friends have the same issue, both men and women bring up sex on a first date to try and prove their prowess (and then 9 out of 1o times fail behind closed bedroom doors). Womp womp.

Be authentic

I’m not going to tell you generally what to say, do, or drink on a first date. The same ONE rule leads all of these actions. Be authentic. If you are boozy, get boozed. If you are sober, say that. If you love to dance, invite them to salsa night. If you can only afford a burger and fries, make it fun but be honest.

If they are a good match for you, they will love doing whatever you are into. Trying to anticipate a stranger’s expectations is unrealistic. And making consolations and compromises is important three months into a relationship, but on a first date? That will only lead to deep-seeded dissatisfaction. Ok, that’s a little harsh, but trust that there is someone who loves low-key dates, or not getting hammered. Be confident that you are an amazing person with quirks and someone will love you for exactly who you are. (gushing…. gushing… gushing)

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