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Dating Journal · Oct 6, 2025

The Dating Exchange - Pt. 6

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Sean Davis · Dating Journal

S: Don’t you close your heart to me, Lucy. Ha. I understand completely how you feel though. Having someone definitely keeps the heart warm and it can aid in the healing process. You’ve been through a great deal lately so don’t be too hard on yourself.

Lucy: What’s the difference between a relationship and a FWB deal? Is it just “love” that separates them? As well as the titles of “boyfriend”, “girlfriend”, “wifey”, “bae” or whatever else tickles your fancy? I’m curious because I’m starting to think these situations will inevitably build more feelings and end up failing. Or maybe that’s me just being scared and already trying to run away!

S: Boundaries. A FWB must be armed with some whereas a relationship has none. If someone finds themselves falling in love with a casual acquaintance, there’s a high risk of heartbreak. That’s why you try to limit the frequency in which you spend time with that person unless you have complete control of your emotions. In contrast, communication is paramount to ensure the other party has the same level of control over theirs. If love develops then it’s no longer a clean-cut FWB agreement any longer. It’s not.

Your intuition about the inevitable failure rate is 100% correct when you factor in the building of real feelings. There’s no way to avoid them from materializing forever. Familiarity, companionship, sexual chemistry, etc; begins to create bonds. A FWB can only last for a short blip – weeks, months – and then it’s time to move towards another person or just find true contentment in being single (without actively dating anyone).

These arrangements begin with an end date in mind, either discussed between both parties, or one already has an exit strategy. There’s no other way to navigate it. It’s meant to be fleeting. Think of it as a rest stop or a layover (on your way to LA). It’s not a final destination; just a detour on your way. Keep that in mind. You don’t need to be scared and run away, silly. Ha. Just understand that it’s supposed to be temporary.

I’m not sure if you’re looking ahead but have you given any thought to being truly single? As in just focusing on Lucy without having sex? I know you want the companionship (with sex) right now but how much longer into the future would you want flings and casual encounters? Have you considered taking the time to just enjoy being comfortable in your own skin? Focusing on the woman in the mirror and thinking about what you want for your next chapter.

Lucy: I feel like I already royally screwed up my FWB situation. We didn’t set any boundaries!

S: Oh, man. OK. Let’s hear it all.

Lucy: Last night walking around the city after we went to a whisky bar, he held my hand - and I let him, and enjoyed it. (Insert awkward, confused face).

S: (Inserted)

Lucy: I’m not sure what we’re doing but I’m having fun, so that’s all that counts right?

S: If you’re enjoying it, Lucy, then ride the wave. You deserve it. Don’t beat yourself up but understand that you’re entering emotional territory that may cultivate bonds you may or may not be ready for. If you’re comfortable and he’s treating you with respect, there is nothing wrong with the happiness you’re feeling.

Lucy: I gave thought to being single as soon as I realised I was happy being single! I didn’t expect to meet anyone. I was just having fun, chatting, flirting, etc. This guy just sort of came out of nowhere, and now I’m just going with it to be honest. I am just focusing on myself first.

I have my priorities in order still. He’s just like a bonus on top of me just being me, being happy with who I am. It is what it is for now. I feel like this guy is still a bit hung up on his ex. I’m just a rebound and no doubt it will end sometime in the near future, so in the meantime I’m going to enjoy it while it lasts, and not expect anything to come from it.

How many FWB have you had? And when they inevitably ended, how did you feel?

S: Answering that question could be rife with all kinds of reprisals. Ha. How many? The line becomes blurred due to the fact that feelings ruined every one of them. Let’s say that it’s been several as the majority of the women I’ve dated have been casual in nature. When I’m entering a partnership labeled with the FWB tag, I don’t feel anything at its conclusion. I’m robotic that way.

I know what to expect from the start and I know it’s going to burn out in the near future. They’re solely based on sexual chemistry so I had no emotional attachment at all. I don’t allow myself to build or yearn for a deeper connection. Once they expired, I went on with life as if nothing happened because in my mind nothing really did. It was just a lot of sex; hopefully it was of the top-notch variety. From that point the only inconvenience revolved around recruiting a new FWB because eventually I’m going to desire another woman – and NO man wants to lose access to consistent sex. Most women make that shit hard to nail down – literally – so tracking down a replacement is a chore.

March 8, 2016. This is a journal entry.

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