When I moved to Sarasota from Chicago nearly a year ago, I had no idea what dating in a smaller city would be like. Back in the windy city, I barely ever ran into former boyfriends or “the group” except for that one Halloween when I dressed as an U.S. Olympic gold medal gymnast clad in tights, chalk, glitter, and a leotard. Yes, the first time I saw his best friends post-breakup I had no pants on. Alllllrighty then.

I started out in Sarasota pretty naïve, yet have quickly learned that any excursion has the possibility of bumping into someone I know.

Here are the top 4 people you will likely run into while dating in a less populous environment (aka Sarasota.)

Your Mom

It was a hot summer morning and my date planned a unique outing – we met at the Farmers Market, had breakfast at C’est la Vie (good taste), and then cruised to St. Armands Circle. There was an art fest and whom do we run into, naturally, but my mom. Poor guy, our first date and he’s already meeting the parents. Small city daters beware, if you weren’t planning on keeping your parents privy to your dating life, you better be prepared with the spiel on your date…where is he from, what does he do, where does he live, what is his family like, what’s his relationship history, where did he go to school, etc. You know how the 20 questions goes. Later she told me “he was so cute!” No pressure.

Your former boyfriend (FBf)

The first post-breakup run-in (PBRI) is always the most startling. The chances of him seeing me at 7:30 a.m. at the farmers market were slim to none, as were the chances of an awkward sweaty gym hello since we went to different gyms. This was a relief for me, because obviously one does not want to be seen in workout clothes, with bed head, or minimal makeup save for a little lip shimmer. Yikes.

Luckily for me, the first PBRI was at chic Social, when I was wearing my black leather over-the-knee hooker boots – hey don’t judge me, they were my dating ensemble essential in frigid Chicago winters – a black leather skirt, and a ¾ sleeve low-back stripped top. It was probably the best PBRI outfit I have ever managed aside from the aforementioned pant-less gymnast feat. Thank you Sarasota, for this opportunity. I was living up to my high school claims to fame: “Best Dressed” & “Most Unique Fashion Sense”. Yeah, double threat.

Anyway, FBf walks in with his entourage and upon noticing, I say hi to his posse, we hugged and then I left shortly after. Since the first PBRI there have been several more FBf sightings (but that outfit has yet to be beat) and each time it feels less awk. Whew.

A guy you are seeing, at a party, with another chick

Ah the ambiguous early stages of dating…no expectations have been set yet and you see each other whenever you have a chance – unless, apparently, if you have a chance to see another girl. Hey all’s fair in love and war. I was wearing a red Anthro dress and strappy shoes (what a great outfit, thank GOD) when I spotted them. I quickly brought my brother up to speed on the situation just before the introductions were inevitably upon us. As the men talked trucks and the guy told a funny story to impress/charm us all, I found myself unimpressed with his date. I wondered what was going on in her brain? Was there anything upstairs!? As soon as his hilarious story ended I politely bid the young’un date and guy farewell. Seeing them and meeting her was helpful intel. Time to move on.

Your coworkers

Fab Louie’s Modern, bad first date. I was wearing jeans, a black, off-the-shoulder shirt, and my blue peep-toe heels. Set-ups, while well intentioned, have the odds of a coin toss. This one was all tails, my friends. As two of my coworkers entered the bar I hopped to my feet and introduced my “friend” to them. Of course, the next day at work I was prepared with a revised, much more condensed version of spiel (see #1). “He was so nice, our lifestyles and interests are just too different.” I was willing to remain open minded about the binge drinking stories – hey, everyone parties – but not working out like ever is just too much of a leap for me to make. GTL or bust.