I Went On Many First Dates In One Day & It Was The Best Decision Ever


Going on just one date can seem like an overwhelming experience. But going on many first dates in one day? That can easily inflict a full-blown anxiety attack.

It used to take me a full 24 hours to prepare myself, mentally, for a date. I would stalk the person's online dating profile or Google results and think of a list of questions to ask on the date to avoid any awkward silence. I would look at myself in the mirror and practice exactly what I was going to say in my "elevator pitch" voice when the guy would ask me what I did for a living, since my job as a professional bridesmaid is anything but usual.

I'd even give myself a pre-date pep talk where I'd remind myself not to say anything too embarrassing or awkward. Don't tell him about the time you ate pizza for 30 days straight, I'd tell myself, so I didn't look like a complete anti-health addict. Don't talk about the time in second grade when you peed your pants and had to be sent home early, I'd tell myself, because that always seems to be a story I somehow squeeze into conversations on a first date.

Sitting in front of a complete stranger can feel scary. Then, having to answer questions about yourself and ask the stranger about themselves can feel like you're at an unattractively drawn-out job interview. Plus, you're supposed to be on your best behavior so that you don't scare the person away so fast, and that alone can be exhausting.

So as a way of helping me get over my first date fears, and as a way of putting myself out there so that my chances of meeting someone great go up (because the chances of meeting someone great by spending every night on my couch watching Netflix is very low), I decided to go on four first dates in just one day. Here's how it went.

Date #1

I picked a Saturday for all my dates. It allowed me to schedule the dates throughout the day with time in between to unwind, take deep breaths, and stuff myself with food, since most first dates I went on were for liquid only.

The first date was at 10 a.m. Yes, I know that's wickedly early for a weekend date, but I had a quota to meet and that meant starting the day early.

His name was John, and we'd been flirting back and forth on a dating app for two weeks. I bit the bullet and asked if he'd like to walk along the east river on Saturday morning. He agreed, saying that he'd like to meet for coffee first so that we'd both be awake for our early morning first-time meeting.

I thought that was a nice gesture, and I met him at a coffee shop on 1st Avenue. The second I walked in, I felt misled. He looked nothing like his photos. It was as if he used photos from six years ago or had someone Photoshop them.  I wish this wasn't a big deal, but it was. I was attracted to someone who wasn't standing in front of me. Not only that, but when I arrived at the coffee shop, he had already bought his own cup of Joe and didn't offer to pay for mine.

I knew I had to get out of this date fast, so I told him it would be best to skip the walk and sit down and chat. I wasn't feeling nervous — I was feeling anxious to wrap this up so that I could go home and change out of workout clothes for date number two.

I drank my decaf cup of coffee in five sips, excused myself to the bathroom, and came back to tell John that it was great to meet him, but I didn't want to take up his whole Saturday. (I also knew he had a lot of plans — he told me the day before he was planning on spending the rest of the day with his college buds.) He had no idea that I had three other dates to go on that day, but I grabbed my purse and made a motion to leave.

He was a little taken back, asking if I'd like him to walk me home. I thanked him for offering, but declined. I hugged him goodbye before either of us had both feet out the door and power-walked my way home.

The date ended up being less than 30 minutes.

Date #2

For date two, we met at another coffee shop near my apartment. I got there five minutes late to test to see if he'd wait for me before ordering coffee. When I arrived, I was feeling nonchalant about the date, since my morning started off with a first date that was quick and didn't leave me feeling bad about not being interested in the guy.

I walked into the coffee shop and saw my date sitting at a table, waiting for me. He looked like his photos, and I was instantly attracted to him. He hugged hello and asked me what I wanted to drink. He took my order (a double espresso) and I took a seat.

His name was Matt and he was 10 years older than I was. I didn't think that would be a problem, but I soon learned it was. When I told him about my job as a bridesmaid for hire, he rolled his eyes. He was a lawyer and his advice to me was to get a "real" day job so that I wouldn't be out on the streets when my business went bankrupt.

I drank my shots of espresso in one swoop and then unleashed a defensive monologue explaining how the millennial mindset on entrepreneurship and side-hustles is the future. I practically showed him my business plan and announced how much money I made that year. He looked uninterested the whole time, and he made me feel as though he wished I had a normal job and worked out of a cubicle from 9 to 5 and came home, ready and willing to entertain him.

We were 37 minutes into the date when I decided it was time to go. I thanked him for the coffee and for his comment in a snarky way. Before I could finish my sentence, he put the sleeves of his coat on, shook my hand, and walked out the door.

Date #3

I was glad date two was over. And while I was feeling defeated, I was feeling ready to see what date three would be like. At this point, dating stopped feeling like a nerve-wrecking experience, but like something I could do on autopilot and be perfectly fine.

Before I left date two, I ordered myself another shot of espresso. I had an hour to kill before meeting date three for lunch at a pizza place, and I needed the caffeine to feel fresh and restored before the next guy.

Lucas was my third date. We got to the pizza place at almost the same time, and we hugged hello outside. He, too, looked like his photos and had a big, welcoming smile. I was excited for our date, but even more excited for my first meal of the day: pizza.

The date started off well. We agreed on a large pizza with toppings we both loved, and then began talking about summer travel plans, since Lucas mentioned he just got back from a Europe trip. We seemed to have a lot in common, from our love of adventure to the books we read so far that year. He was easy to talk to and when the pizza came out, I didn't feel self-conscious eating it in front of him. I even somehow told him my pee story from second grade, and he laughed.

We spent an hour and a half together before he asked for the check. I was glad the date was ending because I was starting to yawn from date-day exhaustion and my need for a nap. I hoped to see Lucas again for a second date and when we walked out of the pizza place, we hugged goodbye and he said to me, "I had a great time, Jen. I'd love to see you soon." My body tingled with excitement. I kissed him on the cheek and said, "I'd love that."

I practically danced the whole way home, where I was going to force myself to nap before date number four. I was so pumped after meeting Lucas that I almost canceled date four. I felt so proud of myself for doing this whole crazy four-date experiment and wanted to brag to my friends how it only took three dates for me to find someone who I was goo-goo eyes for. But I didn't.

Date #4

I napped for thirty minutes, woke up, showered, and prepared to meet date four at a wine bar in the East Village for a quick Saturday night drink. I told him I had dinner plans (which I didn't) as a way to keep the date short and sweet, just in case it was a doozy.

I put on high-heels for date four, because I was feeling so wonderful from the end of date three and excited to finish up a day of first dates. I usually wear converse or beach flip flops (because my style is very laid-back), but tonight was different.

When I arrived at the bar, I was feeling energized. My date, Seth, was already at a table, with a bottle of red wine beside him. I'm a white wine drinker, but I decided to suck it up and not make a big deal about it. Though I did think to myself, Lucas would never do such a thing!

We hugged hello and he seemed a bit low-energy when he saw me, as if he was expecting me to look differently. I'm wearing heels! I thought to myself when I saw his dull reaction. This is as good as I get!

He poured the bitter red wine into my cup and we started talking about our day. He asked me what I did all day and I said that I hung out with a lot of friends. I kept it vague. He told me that he helped some friends move, which I thought was kind and very sweet.

We then started talking about dating and how awkward it can be. I laughed and told him that I didn't think dating was awkward at all! Who had I become in the last 24 hours? He laughed back and said it's weird for him because he just got out of a three-year relationship with someone he thought he'd marry until she cheated on him. That story ate up our hour together, and I was thankful it did because that meant I didn't have to talk much.

I was tired at this point of making conversation with people I didn't ever want to see again. Seth was one of those people. His relationship ended last week; I wasn't going to be his quick rebound, and I wasn't looking to process and handle with care his baggage.

The check came and I didn't offer to pay. I felt like since he made me into his therapist for the hour and ordered the bottle before I even got there, this should be his treat. We hugged goodbye and he leaned in for a kiss. His lips ended up on my earlobe and I laughed. What a way to end the day.

We went our separate ways and I immediately texted my friend Jess. "Jess, OMG." I wrote to her. "I went on four dates today! I know, I'm crazy. But it was great. I kept them short and sweet and out of the 4, there was 1 I'd like to see again. That would have taken me four months to find out if I didn't force myself to go on these dates."

It was a great experiment in the end and I'm glad I did it. Spoiler alert: I never heard from Lucas again. I was bummed for a while, but figured he was one of four, and there were more people to meet in this world and I wasn't going to let him stop me from doing that.

My first date fears weren't totally gone after this experiment, but they were way less. I'd show up on future dates not on the verge of a panic attack, and I felt more in control of conversations, date end times, and even my own confidence. Going through four dates in one day with mostly blah-worthy guys didn't make me lose hope; it made me realize that for every three not-so-great dates, you might get one or two that are awesome, and even if a relationship doesn't blossom from those dates, you'll still be able to see that inside of you, there's that spark of love ready to be ignited.

However, I was going to cut back on the coffee dates. The caffeine was starting to make my heart beat way too fast for the wrong people.

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