I'm a 27-year-old living in Hawaii and I went on dates with 5 people last month. Here's how they went.

·16 min read
Screenshots of two dating app profiles with Ashley posing in the middling wearing a black shirt and jean skirt
Dating in Hawaii is a particular experience.Ashley Probst
  • I'm a 27-year-old dating in Maui, Hawaii, who's looking to form meaningful relationships.

  • I went on five dates in June, but none of them led to a lasting romantic connection.

  • I still made two new friends, but now I'm burnt-out and need a break from dating.

After ending my last relationship about two years ago, I embarked on a year of solo travel, during which I went on a few casual dates.

Now I'm 27 years old and have moved back home to Maui to build a life here and make more meaningful, long-term connections.

Dating on an island may seem like a romantic dream. Most of my friends are in relationships, and Maui is a popular honeymoon destination, so I'm often surrounded by couples. But many singles, including myself, have become jaded after wading in the shallow pool of potential partners.

Trying to find a match in your small hometown is difficult enough — you tend to already know most of the locals — but since mine is also a tourist hot spot, I meet a lot of transients who are only seeking short-term flings.

When it comes to a romantic partner, I'm looking for emotional, mental, physical, and spiritual compatibility — my four pillars of a relationship.

Persisting nonetheless, I went out with five people in June. Here's how they went.

Author's note: Names have been changed for privacy reasons.

I met 4 of my dates on Hinge and 1 on Bumble

Screenshots of Ashley's hinge profiles with a voice note and prompt
A glimpse of my Hinge profile.Ashley Probst

I've been on and off dating apps since I first joined Tinder in 2014, with two serious relationships in-between.

I've also been exploring my sexuality. I identify as pansexual — I'm attracted to people regardless of their gender identity — but have limited experience dating people who aren't cisgender men. I think apps like Hinge and Bumble make it a lot easier to connect with other queer people.

Screenshots of Ashley's bumble profile with photos and bios
A glimpse of my Bumble profile.Ashley Probst

I prefer Hinge since Bumble requires women to send the first message, and if someone doesn't say anything within 24 hours, the match expires. This can be inconvenient if you don't regularly check the app.

Hinge allows users to approve or deny likes at their convenience, and there's no time limit for messaging first. I also like that it offers photo and voice prompts, so people can get more creative with their profiles.

Date 1: We met for drinks on the beach at sunset

After a week of swiping and making tentative plans, I finally met up with one of my Hinge matches.

Once a day, the app allows you to send a rose, which is meant for people you're exceptionally interested in. Zach came up as a suggested standout, so I sent him one.

We started talking and he asked me on a date within the first few messages. We planned to have drinks on the beach during sunset at Secret Cove in Mākena.

A photo of secret cove beach in hawaii
Secret Cove is an idyllic beach setting for weddings, photo shoots, and romantic dates.Ashley Probst

I didn't realize he was 23 years old — which felt a bit young for me — until after I'd made plans. Still, I decided to give him a chance.

On the day of the date, I wore a black crop top and a jean skirt with blue-and-white awning stripes.

Ashley posing while wearing a black crop top and a jean skirt
For my first date, I wore a black crop top and a jean skirt.Ashley Probst

Since I hadn't eaten much that day, I stopped at Safeway for snacks like cheese and crackers, vegetable sticks, and pretzels with spinach-artichoke dip.

I was hoping we might go somewhere for dinner after the sunset but we didn't.

Ashley carrying some snacks to the beach
I picked up some snacks to bring to the beach.Ashley Probst

I arrived five minutes early, and Zach got there right on time.

When he walked down the beach, my first thought was that he didn't look exactly like his photos. I wasn't expecting him to have a beard, but I like facial hair, so it was at least a pleasant surprise.

We found a spot at one end of the small beach and sat on a towel with our refreshments.

View of secret cove beach at sunset, with sand, water and palm trees
Secret Cove was crowded until after sunset.Ashley Probst

We spent most of our time together talking. We discussed my spiritual practices as a professional tarot reader and witch. I also learned that he was interning at a law firm and would be returning to California at the end of the summer.

I had a nice time, but I probably won't see him again

Once the sun had set, we ended up alone on the beach, and he kissed me. It was nice but didn't convince me the connection would be worth pursuing further. Even though we were in an incredibly dreamy setting, I didn't feel a romantic spark.

We still exchanged numbers but have only had one brief text conversation that didn't include making plans to see each other again.

Final verdict: Even though our conversation was stimulating and the kiss was nice, we both admitted to having walls up since he's only on the island for a short time.

Date 2: We also enjoyed drinks on the beach, then went out to dinner

The day after my first date, I went out with Will, a 25-year-old kayak guide and videographer who I also met Hinge.

He sent me a rose and complimented my voice, as my profile includes an answer to the voice prompt "I know the best spot in town for." My answer was food.

We both live in Lahaina, so we met at a local beach park. I almost wore a black dress but predicted it was going to be windy, so I changed into high-waisted jeans and a black crop top.

Ashley posing in front of wooden doors in black crop top and ripped jeans
I wore black crop top and jeans for my second date.Ashley Probst

I arrived a few minutes behind schedule and initially felt bad — until he was 15 minutes late.

His profile included a picture of his two dogs, and I was pleasantly surprised he brought them on our date. They're a distinctive pair, so I actually recognized them before him.

A view of the dogs on the beach at sunset
My date's dogs played on the beach while we watched the sunset.Ashley Probst

Upon first saying hello, I felt like we were old friends catching up after not seeing each other for a long time. It was refreshing to feel comfortable right away, but this didn't foster a romantic connection.

After sunset, he asked if I wanted to get dinner, and I said yes. Referencing my voice prompt, he said, "So miss 'I know where all the restaurants are,' where are we going?"

I wanted a burger, so I chose Cool Cat Cafe, which has a 1950s-diner aesthetic and a decent vegetarian selection.

He had to go home to drop off his dogs and feed them before coming back out, so I went to the restaurant to get us seats at the bar. I ordered a beer to enjoy while reading my book — I always carry one in my bag just in case.

Once he arrived, we jumped right back into a lively conversation and ordered food. I got the Duke la Lanne, which is a vegetarian version of my go-to barbecue burger.

A burger and fries and drink on counter at restaurant
I always get the Duke la Lanne at Cool Cat Cafe.Ashley Probst

During our meal, Will shared that he has cystic fibrosis — an inherited disease that damages the lungs and digestive system.

Even though I didn't see our relationship progressing to the point of children, I still took a mental note because I have a gene variant for cystic fibrosis. I don't have the disease, but if I reproduce with someone who also has this variant, our kid can have it.

We both agreed we connected better as friends

After we ate, I went to the restroom. He paid for dinner while I was gone, which was sweet, but I felt bad because I wasn't sure if we were on the same page.

We weren't romantically or genetically compatible but had good banter and laughed a lot, so I was open to being friends.

We've texted a bit since our date, and I've expressed my desire to hang out again as friends, which he was receptive to. We agreed about not feeling a romantic spark.

Final verdict: Even though we had a good conversation and even better banter, neither of us felt a romantic connection.

Date 3: I spontaneously met up with him at the beach, and we hung out for a while

When I first matched with Brian — a 26-year-old musician and bartender — on Bumble, we bonded over how he had just moved to Maui from Vancouver, Washington, since I had just worked a tarot-reading event there.

He told me he had an interesting tarot-reading experience and wanted to meet for a hike or drink to tell me the story. We planned to connect that week, but after two consecutive dates, I didn't have the energy and asked to reschedule.

A few days later, he sent me a video message, and I recognized his surroundings. He confirmed that he was at a beach that's walking distance from my house, and we spontaneously met up.

I threw on a fun, colorful dress with eclectic patterns, which matched the vibe of the shirt he was wearing in the video.

Ashley wearing a patterned, colorful dress
I opted for a colorful dress.Ashley Probst

We hung out on the beach, talked, and enjoyed some refreshments. He also played a few songs on his guitar, and we sang.

We bypassed small talk and dove into personal topics, like our past dating experiences. Brian told me that he's demisexual, which means he needs to establish an emotional connection with someone before he's comfortable being intimate.

After talking for a couple of hours, we simultaneously had the idea to play pool, so we walked to a dive bar called Spanky's. We ordered drinks and played two games of doubles, which we lost.

We started to get hungry, but the kitchen had already closed, so we went to one of the only nearby places with late-night food, Lahaina Sports Bar. It was pretty crowded, but we managed to snag seats at the bar.

A blue plate of drunken noodles at restaurant
Lahaina Sports Bar offers late-night food, like Thai drunken noodles.Ashley Probst

It was karaoke night, so Brian signed up for a song while I ordered our food: Thai drunken noodles with tofu and Mongolian beef for me and him, respectively — plus another round of beers.

We also had our first kiss at the bar. I later asked him about this since he's demisexual, and he said we had established a strong enough connection for him to feel comfortable moving into physical territory.

After we finished eating, he said he wanted to dance, so we went to a whiskey bar called The Dirty Monkey. It was closing early, but the staff still let us in for a night cap.

a cocktail in glass on granite counter at bar
I ordered an Old Fashioned at The Dirty Monkey.Ashley Probst

I didn't want our date to end, so I suggested that we go to the beach to stargaze. We lost track of time while we talked, listened to our blended Spotify playlist, and kissed a bit more.

The connection has since fizzled out

We've gone out two more times, but I've become skeptical about his true intentions and feelings.

Since our last date, we've only briefly messaged and he hasn't asked to see me. It seems like something has changed, but he hasn't communicated this.

Final verdict: Our conversations were engaging, and we have excellent physical chemistry, but now I've formed an emotional wall.

Date 4: Our short meal was really awkward

Though I felt a connection with Brian, I wanted to continue testing the waters, so I got back on Hinge and met John, a 35-year-old painter.

He asked me out to dinner instead of drinks, suggesting Polli's Mexican Restaurant.

I was going to head there right after work, so I picked a light-blue babydoll dress that worked for my job and the date. It felt a little fancy for such a casual restaurant, but I prefer to be overdressed instead of underdressed.

Ashley wearing a light-blue babydoll dress
I felt a bit overdressed wearing this dress to a casual eatery.Ashley Probst

I showed up on time, and John had already gotten us a booth, as well as chips, salsa, and guacamole.

After greeting him, I intuitively knew that we weren't a good match but figured we could still enjoy a nice meal and conversation.

The interior of a Mexican restaurant in Hawaii
The interior of Polli's Mexican Restaurant in Makawao.Ashley Probst

We sat in uncomfortable silence. He stared at me for some time before finally saying, "You actually look like your pictures." I said that I hoped I did. Then he asked if he also looked like his, and I lied when I said yes.

I knew that he was in his mid-30s, but his photos made him look much younger. His profile also only included shots of him wearing a hat, so I didn't know he was bald. Neither is inherently a turn-off, but the photos definitely didn't represent his true appearance.

The awkwardness continued throughout our conversation — I felt like I needed to ask a lot of questions and talk to fill the silence.

Plate with fish burrito at restaurant
My fish burrito was excellent.Ashley Probst

The service was quick, so we were only at the restaurant for about an hour.

I ordered a fish burrito that was stuffed with ono and sautéed in garlic butter, which was complemented by a hint of citrus.

We haven't had any contact since the date

I offered to split the bill, and then he walked me to my car, where we hugged goodbye.

We haven't spoken since, and I can't see our Hinge conversation anymore, which means he either unmatched me or deleted his profile.

Final verdict: Our conversation felt forced, so there was no emotional connection, even on a platonic level.

Date 5: I was particularly excited to meet this match for dinner

When I saw Alex on Hinge, I was immediately intrigued by their interest in astrology. My first message to her was about my sun, moon, and rising signs, because we share a couple of placements.

We also graduated from the same university, though neither of us loved our experience.

Instead of continuing to message on the app, we switched to text. I don't normally exchange contact information before meeting someone in person, but I felt comfortable doing so with them. After texting sporadically for a few days, we finally made plans to get dinner at Umi Sushi.

I was especially excited for this date because it was during Pride Month, and I had only been out with cisgender men prior to meeting Alex, who identifies as genderqueer and uses she/they pronouns.

Dating in the LGBTQ community is relatively new to me. I started identifying as pansexual in college and went on dates with a few girls, but it never progressed very far. I started seeing a woman shortly after moving back to Maui, which was the first time I had transcended the friend zone, but that relationship ultimately didn't work out.

It's been difficult to meet other queer people on the island, so I was exceptionally nervous before my date with Alex.

I dressed up a bit more than I did for my other dates in hopes of impressing her, wearing a beige bodycon dress with a vintage jacket that belonged to my great-grandmother, black suede boots, and a matching wide-brim hat.

Ashley wearing a beige bodycon dress, black jacket, and black hat
I dressed up more than my previous dates in hopes of impressing Alex.Ashley Probst

Though I pulled up to the restaurant on time, I had to find parking and arrived a few minutes late. Alex was already at a table, and we were one of the only parties in the restaurant, which made it feel more intimate.

We ordered a few plates to share, including two specialty rolls that incorporated truffle oil, as well as hamachi crudo with ponzu sauce, ahi tuna nigiri, and hot green tea.

Plates of sushi on wooden restaurant table
We ordered a few dishes to share at Umi Sushi.Ashley Probst

We discovered even more parallels within our lives. We were in college during the same time, studied abroad at the same university in London, and took two of the same cultural classes.

Our queer journeys were also similar, and it was a relief to connect on that level.

I ended up in the friend zone

After we left the restaurant, they offered to give me a ride to my car. Before heading home, I asked if they wanted to hang out a few days later, since I was going to be in her area for work. She said yes but needed to see which day would work best.

I left feeling excited about our connection because they had the potential to fulfill all of my pillars.

She's since communicated that there wasn't a romantic or sexual connection on their end, but she'd love to be queer, witchy friends. I agreed, saying that I've been manifesting more queer and witchy friends, so how could I say no to someone who's both?

Final verdict: Even though I felt the potential for a romantic connection — many of our spirtual beliefs align, and I think they're beautiful — she didn't feel the same.

Overall, I did make meaningful connections but now feel burnt out and need to take a break from dating

I've always been what I like to call a "hopeful romantic," and falling in love on Maui sounds like a dream come true — but dating in such a small pool can feel a bit hopeless.

Early in the month, I had already seen everyone in my area and had to expand my radius to include other islands. This is disheartening since I've been in a long-distance relationship before and don't necessarily want to get into another.

That said, I was impressed by how many dates I went on. Even though I didn't find a romantic spark, I'm grateful to have made a couple of new friends.

Though I now need a break from dating. I'm energetically drained and have exasperated that jaded feeling I had at the start, but I also trust that these connections didn't romantically work out for a reason.

I know I'll meet the person I'm seeking one day. Until then, I'll continue to work on myself and remain open to whatever is in store for my love life.

Read the original article on Insider