I’m About To Tell Him I’m Seeing Other People

“It feels sneaky” I said to my best friend over text.

“Well, are you guys exclusive?” she replied, pragmatic as ever.


“Well then, you’re fine. Just don’t tell Jack.”

I was getting ready to go out on a date. I mean, maybe it wasn’t a date. I don’t really know what it was. It was drinks with a friend from out of town who I have feelings for. I can’t really even identify the feelings. They’re not passionate, jump-his-bones kind of feelings. They’re more soft, warm feelings – the kind that you have for someone because, above all, you love talking to them.

Regardless, I was going on a whatever it was, with someone that wasn’t Jack.

Jack, the suitor I have been seeing now for the past month or so, is…uncomplicated. He’s attractive in a surfer guy kind of way and he calls me babe which I have decided I like. He does things like take me on proper dates and calls me to say goodnight. He also (to complicate the matter even more) knows I’m moving in March, something we try not to discuss. My impending move has given us an excuse to not talk about our relationship status really at all, a rare luxury. Why define the relationship when I’ll be leaving so soon? That being said, I have feelings for him. I do.

So why then was I getting ready to go out with someone else? Because Jeff and I have this weird history, this fun standing date whenever he comes in town, and I don’t want to give it up.

I met Jeff at a mutual friends baby shower almost 6 months ago and we hit it off immediately. We spent the night talking, and then talking some more, and have kept in touch ever since. Whenever he comes to town for business, which is frequently, we always make a point to see each other. We text occasionally, checking in on one another mostly. He always asks about my job search, or how my family is. I don’t know how to describe it other than that he’s a good person.

Also, I don’t know why I feel inclined to say this, but we’ve only ever kissed. I think if we lived in the same city, I would like to pursue something more serious, but I have no idea if he feels the same way.

“I’d like to see you if you can find the time!” he texted me last week, considerate as ever.

“I’d love that!” I responded, almost immediately feeling a tiny twinge of guilt in my stomach.

We made tentative plans for Jeff to pick me up and take us to a Mexican restaurant by the beach, a pretty off the beaten path locals’ place. Did I choose it because I knew Jack wouldn’t accidentally run into us? I wish I could convincingly say no, but the honest answer is yes – yes I did.

As I texted with my friend before the date, I couldn’t shake the feeling that I was doing something wrong.

“I don’t know” I wrote. “It just, it feels like I’m being dishonest.”

Nevertheless, I went. I went to the Mexican restaurant off the beaten path and drank IPA’s with Jeff. For two hours we caught each other up on our lives, polishing off three beers each before we knew it. He gave me advice on my pending relocation and I applauded the progress on his current real estate endeavors. We laughed and talked about nothing and everything, everything except Jack that is. He never asked if I was seeing anyone, maybe because he assumed I wouldn’t be there if I was? I didn’t ask him if he was dating either, but I got the sense he wasn’t.

When he dropped me off that night, he kissed me and I kissed him back. It wasn’t a friendly kiss.

“See you next time” I said, as I got out of the car.

“Amazing to see you, as always.” he replied.

He told me he’d come visit me once I was settled in my new city, that he’s excited to have me just a few hours drive away.

Jeff will be back in town in a few weeks and if he asks to see me I can’t say I’ll decline.

I went to bed that night incredibly conflicted. Sure, I hadn’t technically done anything wrong, but I was skating on thin ice. I don’t like to operate on “technicallys.”

“Hope you had a fun night!” Jack texted me, as I was drifting off to sleep.

“Thanks honey” I replied. “I’ll see you tomorrow!! Excited to see you!”

As I laid in bed, I wished that I could be okay with the situation, but I just didn’t have it in me. That night I came to terms with the fact that, if I am going to continue seeing other people, I need to set the record straight. I need to tell Jack that we’re not exclusive, because if it was me, I’d want him to do the same. I’d at least want the opportunity to make a decision on whether or not to continue in the relationship.

I know there are “rules” in this kind of thing, and that I’m in my 20s so “I should date lots of people!”, but ultimately I think the gut knows best. My gut is telling me that it is disrespectful to see other people without at least clearing the air with Jack, even if technically until we’re exclusive I can do what I want.

Here’s my predicament, however. I know what I have to do – but god I’m dreading it! I am dreading the moment I turn towards him in the passenger seat of his car, clear my throat, and say some version of “so look, I want to talk about something”.

This won’t be the first time I’ve been on either the giving or receiving end of this conversation. It’s a dance I know well. I always thought, though, that I hated the exclusivity conversation because I hate the ultimatum: leave or fully commit. This time, upon having looked more closely at the actual driver of my hesitation, I have realized that’s not why I don’t want to have the talk.

I’ve realized (somewhat ashamedly) that I’m dreading telling Jack that I’m dating other people because I don’t want him to be okay with it.

I’m not afraid that he will break up with me, or that he will demand we date each other exclusively. I’m afraid he will turn to me, smile, and say, “Okay! That’s fine!”

I’m afraid, deep down, that he’ll give me exactly what I want – an agreement that we can date other people – because then, I’ll feel less wanted.

This is not a particularly attractive sentiment to admit, but it’s the truth. Don’t get me wrong, I know the double standard of the whole thing is outrageous. But when it comes down to it, I want to be able to date other people and I don’t want Jack to be okay with it. Isn’t that horrible?

I don’t want Jack to shrug his shoulders and be unconcerned with the fact that I’m playing the field, because if he is, then I’ll feel like he doesn’t really like me that much. And that, my friends, is my ugly ego running rampant in a selfish way.

It is the truest embodiment of wanting to have my cake and eat it too. I want to date as I please, but all the while know my partner is so infatuated with me that it makes him sick to think of me with other men.

If he responds with “babe it’s fine, you can see other people” I’m going to want to stomp my feet and the voice in my head will scream “but doesn’t it make you mad that I’m not off the market? Don’t you want me all to yourself?”

Coming to terms with this realization feels gross. It’s like looking at a part of myself that isn’t so pretty – it’s recognizing that my ego is far more present in how I confront relationships than I care to admit.

But here’s the thing- I can’t have my cake and eat it too. Not in fair relationships, anyways.

So, I’m going to do it tomorrow. I’m going to tell him how I feel, and in a perfect world he understands. He’ll agree that an exclusive relationship is unrealistic before I move. But if he does agree, I have got to swallow my pride and accept that my feelings are going to be illogically hurt. That maybe, probably, he’ll see other people too. I’ll be upset that he doesn’t want me all for himself, even though I don’t want him to want that.

I guess the only other consideration is that, in fact, that is exactly what I want. That I want Jack to give me an ultimatum, that I want him to say he wants me all for himself. Is it possible that I’m craving the exact exclusivity I’m pretending to reject? If I feel so vulnerable about losing Jack’s attention, or seeing him with other women, then could that mean that I want to be with him and only him?

No. No, it can’t. Because I know myself, and in a few weeks I’ll be back at the off the beaten path Mexican restaurant with Jeff.

Dammit, I’ve got to tell Jack. Being honest sucks.

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Life is messy, let's get dirty.

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