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 27 years old and I'm looking for a relationship.

  • I went on five dates in June, but none of them resulted in a relationship.

  • I need to take a break from dating because I'm burnt out.

I embarked on a year of solo travel after my last relationship ended two years ago.

I moved back to Maui at the age of 27 to build a life here and make more meaningful connections.

It seems like a romantic dream to be on an island with someone. Maui is a popular honeymoon destination due to the fact that most of my friends are in relationships. I have become bored after wading in the shallow pool of potential partners.

Since my hometown is also a tourist hot spot, I meet a lot of people who are only looking for short term flings.

My four pillars of a relationship are emotional, mental, physical, and spiritual.

I went out with five friends in June. How did they go?

Privacy reasons led to the change of names.

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 for the last three years, with two serious relationships in between.

I've been looking at my sexuality as well. Pansexual, I'm attracted to people regardless of their gender identity, but have limited experience dating people who aren'tcis gender men. It's easier to connect with other queer people with the help of apps.

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

If someone doesn't say anything within a day, the match is over. If you don't check the app frequently, it can be inconvenient.

Users can approve or deny likes at their discretion, and there is no time limit for messaging. People can get more creative with their profiles if they use photo and voice prompt.

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

I met up with one of my matches after a week of waiting.

You can send a rose once a day if you're really interested in someone. I sent him one because he was a suggested star.

Within the first few messages, he asked me to go on a date. We were going to have drinks on the beach in Mkena.

Secret Cove is an idyllic beach setting for weddings, photo shoots, and romantic dates.Ashley Probst

After I made plans, I realized he was 23 years old. I gave him a chance.

I wore a crop top and jean skirt on the day of the date.

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

I stopped at Safeway for some snacks since I hadn't eaten a lot that day.

We did not go for dinner after the sun set.

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

I arrived five minutes before the scheduled time.

He didn't look like his photos when he walked down the beach. I was not expecting him to have a beard but it was a pleasant surprise.

We sat on a towel at the end of the small beach after finding a spot.

Secret Cove was crowded until after sunset.Ashley Probst

We talked most of the time. We talked about my work as a tarot reader and witch. He was going to return to California at the end of the summer after he was an intern at a law firm.

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

He kissed me after the sun had set. It was nice, but I didn't think it was worth pursuing further. I didn't feel romantic even though we were in a dreamy place.

We haven't made plans to see each other again since we only had one brief text conversation.

We both admitted that we had walls up since he is only on the island for a short time.

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

On the day after my first date, I went out with Will, a 25-year-old kayak guide and videographer.

My profile includes an answer to the voice prompt "I know the best spot in town for" and he sent me a rose and compliment. I said food.

We met at the beach park. I almost wore a black dress but thought it was going to be windy so I wore a black crop top.

I wore black crop top and jeans for my second date.Ashley Probst

He was 15 minutes late and I was a few minutes late.

I was surprised that he brought his dogs with him on our date. I recognized them before him because they are distinctive.

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

After not seeing each other in a while, I felt like we were friends again. It was nice to feel comfortable, but not a romantic connection.

He asked if I wanted to eat after the sun set. He asked, "So miss 'I know where all the restaurants are,' where are we going?"

Cool Cat Cafe has a 1950s-diner aesthetic and has a decent vegetarian selection.

I went to the restaurant to get us seats at the bar because he had to leave to drop off his dogs. I carry a beer in my bag just in case while I read.

We ordered food after he arrived. The Duke la Lanne is a vegetarian version of my BBQ burger.

I always get the Duke la Lanne at Cool Cat Cafe.Ashley Probst

Will told us during our meal that he has a disease that damages the lungs.

Even though I didn't see our relationship progressing to children, I still took a mental note because I have a genetic condition. Our child can have it if I reproduce with someone who also has it.

We both agreed we connected better as friends

I went to the bathroom after eating. He paid for dinner while I was gone, which was nice, but I was not sure if we were on the same page.

We were not genetically compatible but we had a good time and I was willing to be friends.

He was receptive to my desire to hang out again as friends after texting a bit since our date. It was agreed that we didn't feel a romantic spark.

Even though we had a good conversation, we didn't feel like 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, he had just moved to Maui from Washington and I had just worked a tarot-reading event there.

He told me that he had an interesting tarot-reading experience and wanted to share it with me. We were supposed to connect that week, but I didn't have enough energy to do it.

He sent me a video message a few days later. He told me that he was at a beach that was a short walk from my house.

The shirt he was wearing in the video matched the vibe of the dress I wore.

I opted for a colorful dress.Ashley Probst

We had a good time on the beach and ate some food. We sang while he played a few songs on his guitar.

We bypassed small talk and focused on our own personal issues. Brian told me that he needs to establish an emotional connection with someone before he can be intimate.

We decided to go to a dive bar to play pool after talking for a while. We played two games of doubles and lost.

We went to Lahaina Sports Bar because the kitchen had already closed and we needed to eat. We were able to get seats at the bar.

Lahaina Sports Bar offers late-night food, like Thai drunken noodles.Ashley Probst

It was karaoke night and Brian signed up for a song while I ordered food that included drunken noodles with tofu and beef.

At the bar, we kissed for the first time. He said we had established a strong enough connection for him to feel comfortable moving into a physical place.

We went to a whiskey bar after he said he wanted to dance. We were allowed in for a night cap despite it being closing early.

I ordered an Old Fashioned at The Dirty Monkey.Ashley Probst

I suggested that we go to the beach to watch the stars. While we were talking, we lost track of time while we listened and kissed.

The connection has since fizzled out

We've gone out two more times, but I'm starting to doubt his intentions.

He hasn't asked to see me since the last time we spoke. He hasn't said something has changed.

Our conversations were engaging and we have good physical chemistry, but now I have formed an emotional wall.

Date 4: Our short meal was really awkward

I returned to Hinge and met John, a 35-year-old painter, because I felt a connection with Brian.

I was told to go to Polli's Mexican Restaurant.

I chose a light-blue babydoll dress for my job and the date because I was going to head there after work. It was nice to be at a casual restaurant, but I prefer to be overdressed.

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.

I knew we weren't a good match but I thought we could still have a good time.

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

We sat and didn't say a word. After staring at me for a while, he said, "You actually look like your pictures." I said that I wanted to. I lied when I said I looked like him.

His photos made him look younger than he was. I didn't know he was bald because his profile only showed pictures of him wearing a hat. The photos did not represent his true appearance.

I felt like I needed to ask a lot of questions because of the awkwardness.

My fish burrito was excellent.Ashley Probst

We only spent about an hour at the restaurant.

I ordered a fish burrito that was stuffed with ono and had garlic butter in it.

We haven't had any contact since the date

He took me to my car after I offered to split the bill.

We haven't spoken in a while, and I can't see our conversation anymore, which means he either surpassed me or deleted his account.

There was no emotional connection in our conversation because it felt forced.

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

I was very interested in Alex's interest in astrology. My first message to her was about my sun, moon, and rising signs, because we share a few places.

Neither of us enjoyed our time at the university.

We switched to texting instead of using the app. I don't usually give out contact information before meeting someone in person, but I was comfortable doing so with them. We decided to go to dinner at Umi Sushi after texting intermittently for a few days.

I was excited for this date because I had only been out with cisgender men before I met Alex, who identifies as genderqueer.

I've never dated in the LGBTQ community. I began to identify as pansexual in college, but it didn't progress very far. I started seeing a woman after moving back to Maui, but that relationship didn't work out, it was the first time in my life that I had moved away from my friends.

I was very nervous before my date with Alex because it was difficult to meet other queer people.

In order to impress her, I wore a beige bodycon dress with a vintage jacket, black boots, and a wide-brim hat.

I dressed up more than my previous dates in hopes of impressing Alex.Ashley Probst

I arrived a little late because I couldn't find a parking spot. One of the reasons the restaurant felt more intimate was because Alex was already at a table.

We ordered a few plates to share, including two specialty rolls with truffle oil, hamachi crudo with ponzu sauce, and ahi tuna nigiri.

We ordered a few dishes to share at Umi Sushi.Ashley Probst

We found more similarities in our lives. We were both in college and studying at the same university in London.

It was a relief to connect on that level because our journeys were similar.

I ended up in the friend zone

They offered to take me to my car after we left. I asked if they would like to hang out a few days later since I was going to be in her area. She wanted to see which day worked best.

They had the ability to fulfill all of my pillars, so I was excited about our connection.

She said that she would love to be a witchy friend, even though there wasn't a sexual connection on their part. How could I say no to someone who was both witchy and queer?

I felt the potential for a romantic connection but 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

Falling in love on Maui sounds like a dream come true, but dating in a small pool can feel a bit difficult.

I had to expand my area because I already saw everyone in my area. I've been in a long distance relationship before and don't want to get into another one.

I was impressed by the number of dates I went on. I'm thankful that I made a couple of new friends even though I didn't find a partner.

I need to take a break from relationships. I trust that these connections didn't work out for a reason because I have exhausted my energy and felt like I had lost my mind at the beginning.

I will meet the person I'm looking for someday. I'll keep working on myself and be open to whatever comes my way for my love life.

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