First Date Pitfalls

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The notorious Chi Serial Dater has done an amazing job keeping her identity under wraps so when I had an opportunity to collaborate with her and find out who the hilarious girl is behind her words, I was more than ecstatic. She has no shame, isn’t afraid to share her ups and downs, and like me doesn’t call herself an expert. She’s a girl who’s not afraid to share her dating successes and conundrums for entertainment purposes, but more importantly so others can learn from her experiences.

I am excited to bring you a list of the top 5 First Date Pitfalls written by the infamous Chi Serial Dater exclusively for fans of my blog. Enjoy, laugh, learn, and if you are a guy in the Second City make sure you step up your first date game because you never know if you might be on a date with this awesome chick!

Here are the Chi Serial Dater’s top 5 First Date Pitfalls:

First off, I’m no expert; I’m just a girl who goes on a lot of dates. First dates, to be exact. I’ve sat through dreadfully long dinners and sipped cocktails across the table from strangers all over this fine city. With more than my fair share of first dates under my belt, I’d estimate I’m about halfway to First Date Aficionado status, quite an accomplishment, if I do say so myself. I’ll be the first to admit that when I agreed to my very first Stranger Date, I was wide eyed, innocent and about as clueless as those kids on Catfish. Out of the game for nearly two years and my most recent girlfriending skills limited to Skype dates (international long distance dating; impossible), my dating capabilities were similar to that of a thirteen year old. But oh, what I have learned since!

When it comes to do’s and don’ts for first dates, all you have to do is a simple Google search etvoila!you’ve got tips of all sorts, ranging from “DON’T eat garlic for 24 hours leading up to the date” to “DO break the dating rules!” Seems like a lot of lists to sift through, so I’m cutting it down and keeping it short(er). Based on honest to goodness, real life experience here are my Top Five First Date Pitfalls that will nearly 100% guarantee that date #2 will never, ever happen:

1. This one seems like a no-brainer but, honestly, it’s absolutely essential: Just don’t make things up. As much as you want to be the type of person your date will like, the only person you can be is yourself (as corny as that sounds.) This is true in all aspects of dating, from the content in your dating profile to the way you present yourself on date #1. My mother always taught me to Begin As You Wish to Proceed and if your end game is a relationship, and the foundation of a good relationship is honesty, well, start with honesty.

Anecdote: I almost felt like I had been catfished when my date showed up and was probably 5 years older and 50 pounds heavier than his profile pictures. Nice try buddy-o.   

2. This First Date Faux Pas I learned from my second-ever Stranger Date. Please, absolutely do not show up with a checklist of Deal Breakers that you’re not willing to budge on without giving your date a bit of a heads up. Nothing will bring a date to a screeching, awkward halt like demanding your date conform to your standards or hit the road. It’s understandable to have a list of mandatory requirements, particularly faith or culture-based, but if you know that’s your criteria and you’ve got no room for flexibility, be upfront about it before sitting her down to dinner.

Anecdote: I was once told I would need to convert to Judaism, start keeping kosher, and have my tattoos removed. On a first date. It was heartbreaking. He was so cute.   

3. One first date pitfall that I begrudgingly admit has been an err of mine in the past is this – as a lady, don’t try to go drink for drink with your date. Personally, if my date is sitting with an empty glass and I’m still nursing my drink, I feel compelled to finish up so as to avoid the awkward – you’ve just lapped me in drinking – thing. But do that too many times and, well, that’s that. That said, if my date is powering through beers at breakneck speeds then we’re probably not hitting things off and that we should probably both do ourselves a favor, end the awkwardness, skip the impending hangover, and call it a night. Alcohol may be liquid courage but nobody needs that much courage to sit through a first date. Patti Stanger might’ve had it right: two drink maximum (even if you’re not trying to date a millionaire.)

Anecdote: To be fair, I had a lot of fun, but when I found myself at a whiskey bar at 1am on a Wednesday night with an invite back to his place; it quickly became clear that this was not a legitimate long-term dating plan. 

4. It’s generally understood that people who are dating online are going on multiple dates, which is entirely acceptable, but it’s important to respect each date for what it is: the opportunity to meet a person you’re hoping to have a connection with. Do not skimp on the details, regardless of how many dates you’ve been on that week/month/year. Do you really want to admit that on your first date with your future spouse, you chose that dive bar down the street from your office simply because it was convenient and you were tired? Plan ahead, pick a spot you’re confident in, choose a place within your budget (doubling up on the don’ts here: don’t go dutch. Just don’t. The person who proposes and coordinates the date assumes responsibility for said date, including reservation-making and tab-paying.) Wine ‘em and dine ‘em a bit or you might miss out on something great.

Anecdote: A date once admitted to picking a somewhat divey bar he had never been to before because it had okay Yelp reviews and easy parking. 

5. In a similar vein as #4, don’t let your discouragement from other dates flow over into new dates. It’s hard not to feel a little bummed out by first dates that don’t lead down the road to eternal bliss, but each first date is an entirely new, completely different opportunity. Be present. Be engaged. Nothing is more exhausting and frustrating (for both parties) than a date with someone who doesn’t want to be on a date. Online dating isn’t for everyone and if it makes you supremely uncomfortable, don’t do it. If you’ve had a streak of bad dates and you’re feeling pessimistic, suck it up, put a smile on your face and give it your best shot.

Anecdote: The single most unpleasant date I’ve ever been on was with a guy who sat, leaning back, arms crossed, sharing nothing and cynically smirking as I floundered to keep conversation afloat by myself. It felt like he was judging me for being there. I went home genuinely exhausted, feeling defeated, and cried.

Joking or serious, the point is that dating should be a true balance between fun and serious. Everyone has their own unique dating style and their personal preferences when it comes to dating, but remember to respect the process and embrace the opportunity. Mind your Ps and Qs, put your best foot forward, keep your mind openly optimistic. Oh, and don’t eat garlic within 24 hours before a date.


Click here to read the Chi Serial Dater’s blog

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Jillian Conley

About Jillian Conley

Author of Maid of Honor, Dating Chase Walker, Time for Audrey Buchanan & the Coffee Table Quotes collection. Blogger giving life advice through stories. Co-founder of My Three Sisters Publishing. TV Host Social Chicago. Radio Host Love Code on Modern Problems Radio Show.

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