Sifting through dating websites, disenchanted by the generic wet rags on boats and golf courses, I lifelessly, monotonously swiped left until I finally spotted an interesting profile of a man named Sean. Unlike the other men showing off their muscles and their fresh catch of the day, Sean had not even one regular profile picture of himself. All the pictures were artistic black and white photos of Tampa landmarks, vintage cars, and stacks of library books he was reading for school. His Tinder profile read, “Artist, history nerd, old car nut, Florida native.” Art, intellect, and an appreciation for vintage culture, exactly what I needed to razz my berries. Swipe right!

Our first date was at a hipster pizza and craft beer restaurant. We had pleasant conversations about his graduate work and his love of Tampa history. We even discovered that we have some mutual acquaintances which helped us to bond a little. However, he also brought a lot of drama to the table discussing his divorce battle and financial problems. I was seeing a lot of red flags, but I enjoyed his conversation, so I considered being friends. At the end of the night, he walked me out to my car and gave me a slithery, lizard tongued kiss goodnight which did not make me tingle.

Over the next few weeks, Sean and I chatted off and on. Even though our first date hadn’t ignited any magical sparks, we definitely enjoyed intellectual banter. We finally decided to go on another date, and our date was inspired by a blog post I found on Facebook called the Goodwill Date.

The Goodwill Date Challenge: You and your date have $10 each to pick out an outfit for each other at a thrift store. You immediately change into the clothes, give each other fake names, and go out to dinner taking on the personas of your fake names.

We hit the thrift store first. For me, he selected an off-white sheer peasant blouse, subtly revealing my black floral bra which he referred to as my “star spangled brassiere,” a fitted grey mini skirt, and black and white geometric heels.  I had brought a few wigs with me, and he chose a sassy cherry red bob to complete the outfit. I was transformed into “Veronica.”

Next, we found his outfit, olive green camo pants, a peach striped button-down dress shirt, and a pair of buttery Florsheim dress shoes that looked to come from a stylish Cubano elder.  Sean transformed into “Eduardo” for the night.

All decked out in our new threads, we hopped into his souped up vintage Thunderbird. He popped open a PBR, took a swig, and brazenly belched . Although I was initially interested in him for his artsy, intellectual edge, he had a raw manly side which was attractive. By the time he finished his beer, we had arrived at our destination, The American Legion. The air was clouded with smoke, country music, and Aqua Net hairspray from all the big haired ladies.  “Eduardo” ordered us two strong drinks, then grabbed my stool to pull me in closer, putting his arm around me. We had a swell time, gabbing about life while guzzling our drinks.

Feeling tight from the screwdrivers, we headed back to his pad to screw around. We retreated to his vintage office where he spun some Dave Brubeck before laying me down on an orange vinyl vintage waiting room chair with a divider between the seats. Sitting like two naughty kids waiting in the office to see the principal, we navigated around that bar for some serious necking.  Our fun was interrupted by my curfew to get back by the time the babysitter had to leave.  Yes, I’m a grown adult, but dating as a single mom throws in challenges that are similar to those of a horny teenager trying to make out as much as possible before dad arrives with the shotgun.

The second date was a blast, and I considered going on a third. Sean and I met one more time for pizza, beer, and snogging. I later found out that he had dated one of my friends and it hadn’t ended well. There is no need to go into the story here, but after hearing the word from the bird, I put the kibosh on it. He tried to contact me a few times more, but I always came up with some excuse why I couldn’t see him. Instead of setting myself up for disappointment, I decided to stick with the memories of our few dates.

Sean reminded me how much I need creativity and adventure in my life, and I kept that in mind as I set up future dates with other men. Dating is much more interesting when we allow ourselves to move past the stereotypical dinner and drinks. Adventure dates open up the door to creativity, add playfulness, and result in much better stories to share. And as I continued to go on more dates, I started to see that those atypical dates also reveal a lot about a person’s character. So, before you set up your next date, think about planning a creative romantic rendezvous. Even if the relationship doesn’t work out, at least you will have some killer experiences to remember.