Hello! Guest Post: The Accidental Dates

Hello it feels like ages since I have blogged but we have been so busy running around town seeing friends and family! Luckily for me, and you, I have an awesome guest post for you today while I collect my thoughts on our first few days back in California.

Eryn from A Proper Fool is going to tell us how to avoid accidental dates! Her blog is seriously one to live vicariously through as it is  filled with pictures and stories of her new life in New York as a fashion intern.


We’ve all been there. Stuck in between too nice and generally clueless. One moment, you’re just minding your own business (a cliche sentiment, I know), drinking a coffee, having a solo drink, or reading a book, when, BAM.

Someone strikes up a conversation. No harm, no foul. We all like to make friends, so the conversation begins with the usual, “Where are you from?” “Are you in school?” “What do you do for a living?”

But, occasionally, these questions can get a little bit more intimate. And suddenly you’re being asked what you wanted to be “when you grow up,” how your parents’ divorce affected you, and what your “hopes and dreams” are. And it hits you. You’re on a first date. And even stranger, a completely accidental first date.

Here we are, my top two accidental first dates:

1. A friend of mine, who had also been close friends (and even went on a couple of dates with) my sister, casually asked if I wanted to grab pizza. It was a rather dreary, rainy Thursday, so of course a warm pie of tomatoey goodness sounded perfect. It really hadn’t occurred to me that he was remotely interested in me (it’s rare that both my sister and I are pursued by the same individual–we both look and act like completely different humans).

So, to dinner we went. He offered to pick me up, I unknowingly relinquished my escape route. We arrived at the pizza place and I assumed we would each buy our own individual pizzas. Because that’s what not-so-great friends do. However, he suggested that we just split the larger size. This also seemed harmless, considering that I generally eat pea-sized quantities.

Then, he insisted on buying dinner. And on us accompanying the pizza with drinks. And finally, he wanted gelato to share afterwards.  Upon realizing the ploy, I was immediately uncomfortable. I mean, who just first dates (yes, this is a verb) someone without asking?! We were in a cozy corner of the restaurant, making incredibly awkward conversation. Post-pizza, I made a mad dash to the gelato counter and insisted on buying the dessert (two separate ones, at that). By the end of the night, we had at least gone dutch.

2. This next first dater, we will call “accidental first date M.” This guy had been a customer of mine while I was working at a coffee shop in college. A generally nice and complementing sort of fellow. But I mean, most of the complements were directed towards the drinks I made. So when he said he would come to my fashion show to see the piece I had in it, I didn’t think anything of it. And even when he didn’t have a car so asked if he could ride with me, I didn’t think anything of it.

There we were, both dressed up, on our way to an event together. He did make an effort to open doors for me, but that’s pretty common in the South, so no red flags. On the car ride there, though, he asked me where I grew up. And about my siblings–how we got along, whether or not they were anything like me, if I missed them…he asked me so many questions that it began to feel like he was really trying to get to know me. I assumed it was a friendship sort-of-thing.

We arrived at the event! After what seemed like an eternity (my knack for getting lost didn’t help), and he did that hand on the small of your back thing. You know the one. The symbol of being at an event with someone. And the next sign that he was “with” me for the evening–he kept telling people he came with me. He told my friends, he told people I only sort of knew…we were there together. I was mildly mortified. He was a nice guy, but I was going through my extra single phase and was looking forward to going to a nice event stag. He didn’t get my hints at that and tagged along to the after party, offered me his jacket because it was unseasonably cold (and, of course, a jacket would have ruined my ensemble). All in all, an okay date. Or it would have been, had I known it was happening. The best part of this story is that he was actual a serial secret first dater. We found out a month or so later that he had a very similar evening with another girl. Kudos to him.

So how does one avoid these completely awkward and unrequested advances? I like to think I’ve become more aware of them as I’ve aged, yet I still don’t know how to kindly and respectfully ask someone to not take you on a first date that they never even asked you on in the first place…but my these little tidbits might at least make the evening move more swiftly–

1. If you think an outing has “first date” potential, probably you should eat something filled with garlic and generally messy to eat–spaghetti. Great choice.

2. Wear extra loose-fitting, androgynous-type clothing. Skip the makeup and perfume for this one.

3. Avoid having more than two drinks, because, as we all know, you’d love to be first dated by most anyone if you’ve had too many.

4. Shorten as many words as possible. Totes obvs you look gorge, but your bff is qter. Via text and in-person.

5. This one is especially important: look as bored as possible. Complain about the lighting, your warm food is too hot and your cold drink is too cold.


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