Ahh hell, I’m going to write it out anyway so I can at least have this organized in some form.

I use “organized” as a loose term.

To shorten this, I’m going to put it into small sections.

The meeting:

You know how people always say you meet the perfect person when you aren’t looking? Yeah, that seemingly happened to me in January. I met this girl as I was leaving the bar. I was putting my jacket on saying goodnight to my friends who work there, and she walks in with her friend, and are seated next to where I was sitting.

She said to me “oh, I get it: we show up, and you leave.”

Naturally, I stayed.

We ended up talking for hours. Discussing anything and everything. On the topic of travel, I mention a wedding in Caribbean scheduled for July. She says, “and I’ll be your date.” I say, “let’s see if we are still talking by May before we book your flight”.

We ended up as the last people in the bar, and to my surprise at the end of the night: she kissed me and invites me over. I work in 4 hours at this point, and I politely decline. We have had plenty to drink, and I didn’t want to disappoint/hurt my work day more than I already had.

We exchanged numbers, set up a date, and ended up talking all week, great banter, and big smiles all around. However, it was all leading up to…

The twist (part 1):

I know, the “part 1” is really building up suspense.

On the day of our date, I receive a text message from her. I gleefully open up my phone, and she is cancelling our date. Honestly, not the end of the world for me… it happens all the time. Turns out, she was in an open long distance relationship, and her boyfriend had decided they should be exclusively together.

I tell her I understand, and I was really excited to keep getting to know her. Felt like we have a great connection, but I totally understand.

Later that day, she texts me again. She is out at a wine bar by herself, and she invites me to join her. As friends, not as a date.

The evening is humorously awkward at the beginning, but as we shake off the initial gitters, we have a great time, open conversation, lots of laughs… it’s a really great… not date.

End of the night, she is making a lot of flirty comments, and eventually we do kiss again. A bunch. Not a date, can’t happen again, we are just…

“Friends who kiss sometimes”:

Over that next month and a bit, we hang out every few days, the kissing only happens a few more times, but we definitely are getting closer. I learn a lot about her, she opens up about her relationships(past and current), we discuss our passions, and encourage each other in all the right ways.

The boyfriend comes to town for Valentine’s Day, and I tell her to “not worry about me, focus on your relationship and be in that moment”. It’s not what I WANTED to say, but it isn’t my place to be selfish.

The boyfriend leaves on February 15th, and she invites me to dinner that evening. I meet her at the restaurant, things are just lovely, and I know my feelings are not going anywhere. After the mains are done, we order dessert(my birthday is the next week), and then…

The twist (part 2):

… She says: “I need to tell you something, and I’m really nervous to say it.”

Uh-oh, I think in my brain. “Hit me, you can tell me anything.”

“I’m an escort”, she says, maintaining eye contact.

It takes a minute for that revelation to land. Not quite sure how to take it, and it makes me start rethinking every moment since I met her.

She encourages me to ask questions, which she knows I inevitably have.

We discuss a LOT of what she does, I ask some questions, and tell her I’ll likely ask her more as they arise.

“I understand if this changes how you view me, and want you to know I truly value you.” Is what she says at the end of the night.

We end up talking more, and keep hanging out. I work a really busy job, so my life is a bit chaotic itself, but we make time when we can.

Work/distance:

I am “deployed” to a small town a couple hours away, so we only have FaceTimes and text messages. There are a million questions running through my mind, but I’m doing my best to triage and mitigate them. Mid March, she tells me she is going to visit the family and boyfriend to “give it a proper shot”. I respect her for this, and encourage her to do so.

At this point, even with all the uncertainty… I’m in. Even with the boyfriend… I’m in. I am infatuated with an escort, and it’s a spot I never pictured myself in. On her last day in town, she calls me late at night and asks me if I can come over. I go over, I help her pack, and the next day she is off.

Over the next couple weeks, we aren’t talking nearly as much as we were. Little check-ins here and there. And one day, on April 21st at 5 in the morning, there is a FaceTime call. I have just started work, she is just getting in from a night out. It was her first time using MDMA, and she wanted to tell me all of the feelings and thoughts.

She told me she loves me, that she is feeling stupid for going back home, the boyfriend isn’t working out, and that she thinks of me all the time and doesn’t want to overwhelm me. I’m actually SO happy to hear this, and I reciprocate. Of course, I take these words with a grain of salt… it is a girl high on MDMA… but it’s nice regardless.

We talk about the Caribbean wedding again here, and she says she still wants to be my date. I tell her, she needs to be single for that date to happen.

She tells me she is coming back for a few days in 3 weeks, and we set up a time to see each other.

The visit:

She comes out for 6 days. She has a couple of work appointments, a concert, and a friends birthday. We have one day we can see each other, so we plan to hang out at my place, cook dinner, and just relax.

So naturally I see her 3 times in the 6 days.

The first time, she calls me at 11pm and tells me she wishes I were there. I hop in the car, drive 1.5 hours, and see her for the evening. Funnily enough, it was the hotel after her “work date”… but I didn’t mind. We had a drink, chatted, and slept together spooning. Not sex, no kisses. Just holding and sleeping.

We have the dinner date, and cook up a storm, swing dance in the kitchen, and watch a movie. Something in the movie made me say out loud “I’d build you a house”. And she replied, “and I’d marry you in that house.”

This time… we definitely got a bit carried away. What started as a small peck, turned into hands all over bodies, rolling around, passionate make outs. But… she is still with her boyfriend. We do not have sex. Which was killer.

I end up driving her to the airport, drop her off, and she kisses me on the cheek goodbye.

The shift:

24 hours after she goes back, she ends things with the boyfriend. She is asking for my advise on things to reply in the texts, and I do my best to assist, but be clear that I’m not the right person to be helping her with this… but I help nonetheless.

Our conversations go from her processing her breakup, to the emotional rollercoaster that was spending time with me, and I suggest she takes a bit of time to focus on herself, and not worry about me(again… I really need to stop saying this…). She says to me, “I don’t want you to wait for me. That wouldn’t be fair to you. I don’t want you to be a rebound.” It is at this time, she says she will not be coming to Caribbean with me. Totally understandable.

I tell her that I agree, and I will not wait. Naturally, I do the exact opposite.

She goes radio silent for a bit, and I keep diving into work. She pops up here and there, and we end up back to a daily text/call routine.

Both of us being single people, she ends up meeting someone, and has a summer fling with them. She is coming back to home early August, so it will be short lived.

The thing is… she doesn’t really tell me about this in our calls and texts. I pick up on it in instagram stories, and various comments. Nothing direct, it feels like she is trying to not hurt me by saying anything.

She ends up going to abroad for a wedding(with this guy), and ends up FaceTiming me FROM the wedding. I’m a bit confused by it, but it’s not a bad sign that she is at a wedding and instead of being with her date, she wants to be with me. She says she wishes she had come with me to Caribbean instead of staying… which leads us to…

The return:

I still do not have the details about what has been going on in her romantic/work life while away. But when she asks me to get her keys from her sublet, and pick her up from the airport? You are damned right I jumped.

I went and got her favourite flowers, and made a joke about being the guy in the airport with a massive sign saying “welcome home!”. We plan to go to dinner at the place we met(8 months to the day), and I set everything in motion.

I pick her up, big smiles, amazing hugs… and then she starts talking about the guy. The feelings built up, and she was sad to have had to end it. We talk about it on the drive home, her holding the flowers(she loved them, by the way, and was shocked I remembered her favourites). When we get back to her place, we cancel the dinner plans, and she goes up to get settled in for the night.

We text a bunch the next day, and late at night she calls me to come over. I drive down (another 1.5 hour drive), and we hang out for a couple hours. She is packing for a “work trip”, for an out of town client. While I am there, she casually changes in front of me. This is the first time I have ever seen her naked. At first, I turn away, as if I made a mistake looking in the first place. Then I let my eyes linger a bit. Her doing this is something that is stuck in my mind however. I know it was intentional, but I’m curious if my reaction was not what she had expected. I am not a rebound. It made me think back to the night we met when she had invited me over…. Had I known that might have been my only chance to have sex with this woman, I probably would have jumped at it. Life is a funny thing.

I drive her to the airport the next morning, and we talk her entire trip(minus a couple hours).

This is where we are at now. I haven’t seen her since she got back, we made plans to hang out… and she has now pushed them to next week.

TL;DR

What the hell kind of mess am I in, and why do I love this woman so much. My logic says that there are too many games being played, and I’m not actually a factor… but my heart is telling me that I am right, and following this path makes a lot of sense.

I’m a good guy, I wear my heart on my sleeve, and I have been catastrophically hurt in the past by women, and yet here I am courting an escort… who wants me but doesn’t. This isn’t confirmed, it is just my current read… she doesn’t want to lose me, but she also doesn’t want to be with me.

The sex worker aspect does not bother me at all. And the fact that she has trusted me with everything(but she has not trusted a boyfriend, ever) is something I hold dear to me.

I have a lot of thoughts, and I know it doesn’t look like I kept this short… but I definitely did. Haha

I don’t feel fully comfortable talking to my regular therapist about all of this yet either. She knows a rough outline, but not the escort part.

This is helpful to get this out on paper. I’m just looking for some opinions/thoughts on the matter, or if anyone has any similar experiences.

Appreciate your time and read.