How To Have Fun While Dating

How To Have Fun While Dating

Disclaimer: I’m still figuring my shit out 

It’s been 5 years since I went on an official date and my last date was a DISASTER.

It was September 2021 and I honestly can’t remember much of it but I do remember lots of intense eye gazing on the date. I don’t remember how riveting the conversation was but I do remember being utterly disappointed the following week after the date.

I also slightly remember something VERY weird happening like him asking me for money or something in that realm?

The date prior to that was with a man from Egypt who greeted me by saying “oh wow you look even better in person” as if I was fugly in the pictures on my dating profile or something.

I think this was supposed to be a compliment but who knows because as we were conversing in his car. he felt the need to point out that I had a lisp. I’d been living with myself for 26 years at that point and believe me my brotha, I know the lisp is there (but I think it’s so cute and I’d always wanted a speech impediment + what makes an impediment an impediment?! What’s a “normal” way of speaking?)

Anyways, I digress lol

Let's rewind a little...

It's 2020 and I’d just gotten out of my tragic toxic two year possessive relationship and the months I’d spent afterwards “dating” were nothing short of a disappointment.

These “dates” consisted of men coming over to my apartment and having sex with me. That’s it, that’s all. Everyone was so disconnected or slightly deranged, it felt… dystopian.

It was as if my home was being used as a motel for folks who were tired of having to hear their roommates and just wanted a peaceful nights sleep. Seriously, a guy spent the night at my apartment after we’d had sex and I’m 99.9% sure it’s because he didn’t feel like going home and hearing his loud roommates that he’d told me about.

And yes. The men that were coming over to my home were random men from an app that I’d never FaceTimed with before meeting or talked on the phone.

Looking back, I’m so grateful I made it out my 20’s alive. Don’t follow my lead kids.

Instead of asking to be taken out on a date, I’d reduced my expectations and started telling men I wanted to be friends with benefits. There could be no disappointments if I kept my expectations to the ground… so I thought.

My Friend With Benefits

That was until I met my FWB (friend with benefits) in 2021. If you’ve read my work before, then you’ve definitely heard the story of how he was the first person I’d ever experienced a true penetrative orgasm with when having sex AND I did this while I was on top of him which was an extra spectacular feat for me.

I didn’t expect us to connect like that sexually and I definitely didn’t expect for us to actually grow a friendship and experience that kind of intimacy together.

Most people I’d been with were terrified of intimacy. They hadn’t met themselves and so meeting me deeply was far from ideal for them.

All of the friends with benefits I’d had in the past were more one sided benefits with zero friendship attached. They couldn’t have cared less about me but that’s because they also didn’t care about themselves and in reality I didn’t care much about myself either.

This friend with benefits was different. Every time we’d have sex (which was only TWO or THREE times) he’d get up, get us water, check on me, ask me how the experience went and if there was anything I needed him to change or improve on, he’d bring me a wash cloth to clean up and would cuddle with me and listen to music after everything was done.

10/10 experience AND he taught me what aftercare was. I’d always craved it. And even if my ex and I did occasionally do that for each other, we hated each other and ourselves so much at the time that the aftercare would be diminished by an intense fight and emotional disconnection. I can’t even really remember us doing a lot of aftercare but it HAD to have happened with the two years my ex and I were together… right?

My experience with my FWB was amazing until… I found out he was actually dating someone. Like taking her on actual dates.

Oh no! Not only was he transparently sharing this with me, because of course, we were friends and that’s what friends do but he was also really excited about her. He’d also given me insight into his previous relationship and she (his ex) was exactly like ME! Nurturing, ambitious, vegan, caring etc.

This was when I realized I’d sold myself short.

I DID want to date and I DID want to explore a deeper connection outside of friends who had sex.

When I eventually shared this with him, he didn’t shut me down but he also told me he hadn’t even opened his mind to that idea because of our initial agreement but I’d only made the initial agreement because I was scared and also couldn’t stand to be rejected by one more person based on me wanting to be cared for (which is crazy to think about now but still I rise.)

Anyways I finished this story on my podcast but now here we are 5/6 years later.

I joined a dating app again and had opened my heart up to companionship. Sometimes I wonder if it’s because I lost my fur companion and soulmate in 2025 but I can’t lie there’s no man or woman (outside of my mom) who could ever replace the kind of unconditional love that she (my cat) provided for me.

So what was I craving?

When I was asked what I wanted by someone on the dating app, I’d say “I want a connection” and would usually say I wanted to go on a hot date of some sort. I wanted to make sure I was being transparent with what I truly wanted.

I wasn’t a booty call and the date wasn’t going to involve me coming to your house to have sex.

But saying I want a connection is a little vague.

Did I want a hot spicy intimate connection?

Did I want a slow loving friendly connection?

Some connections can be trauma based and inorganic? So what was it?

While my brain began to think through what I actually desired…. I met someone.

The Someone I Met

I was planning a trip to LA and I’d matched with someone who was vegan, the convo was cool, we expressed our expectations and we’d officially planned our hot date. He asked me where I was gonna be staying and I hadn’t had that arranged yet so I told him I’d let him know and we moved on with our positive convo.

I was somewhat excited, I didn’t know what we were going to do but it was going to be my first date in a LONG time. I mean 5 years is … a lot. And of course I’d taken myself on many solo dates but that’s totally different (and very necessary!)

I woke up the next morning and didn’t hear from him but I didn’t think too much of it. Who am I kidding? I checked my phone every few minutes while trying to convince myself I didn’t care. Eventually I turned my notifications off and continued on with my day.

That night, still nothing but I did notice he’d changed all of his pictures on his profile. Hmmm interesting but that’s ok people do that all the time.

The next morning….he unmatched me

And believe it or not, I felt RELIEVED. I even celebrated with a dance around my room.

I actually wanted to spend that week celebrating and honoring my fur babies transition since the one year anniversary of her passing and I really didn’t want to spend it around …. A man. Especially not a stranger.

So all in all, the ghosting was divine.

Fast forward to now… I finally feel like I’m ready to make some intentional connections!

My desire is simple: I want to make an organic connection with someone that makes my body feel safe and calm and joy.

I’m more so craving an intimate friendship, friends that get dressed up and go on dates, have intimate conversations and intimate moments physically together that do not always lead to sex.

I actually feel committed to my abstinence and would only move forward with having sex with someone if my body tells me it’s the right time to do so and of course they’d have to meet all of my requirements (getting tested, getting psychologically evaluated jk jk but like… maybe?, being in therapy, being vegan.. I’m serious about that one… the list goes on and on) but this list is important because these are the things that make my body and mind feel safe.

Here are a few more rules I knew wouldn’t change for anyone no matter who I met.

1. We absolutely were not going to have sex until we met every last requirement on my long list of “before we had sex” requirements.

2. We’re definitely not going into each others homes on the first, second or third date.

3. No phone calls until I reeeeaaally trust you and then I can make the time (understanding my time is literally limited and I’ve hated phone calls since I was 16) but FaceTiming before a date is a must.

4. Having a conversation (or many) about consent and what that means to each of us.

5. Having a conversation (or many) about our desires and what makes us feel good.

Those are the main ones at the moment but the list is ever expanding as I grow.

But suddenly… everything started to feel so real.

The CONCEPT of connecting with someone felt amazing but ACTUALLY connecting with someone felt terrifying.

This was the most alive I’d felt in years, the most naturally open my heart had felt, the most present I’d been ever.

When I was dating back in the day I was the queen of dissociation. I couldn’t even recollect half of my sexual experiences because I was dissociated through most of them.

I didn’t want to be but that’s the way trauma unfolds sometimes.

So here I am, present, heart open, with a new perspective and now the idea of dating terrifies me…. Yet I am doing it.

Attachment styles

My disorganized attachment style also makes dating a bit complicated.

My anxious attachment style makes me want to check my phone every two seconds to see if they responded.

My avoidant attachment style makes me want to go away when things get too real.

And my secure attachment makes me want to work through the fear and be brave and have fun.

Addicted to drama

Then you have the actual chemical aspect of getting to know someone.

When I was dating in my 20’s it was constant drama. I used to say I was addicted to pain but I think I was genuinely addicted to whatever emotional adrenaline or cortisol rush I’d feel when the person I was “dating” and I weren’t seeing eye to eye.

It’s all I knew.

I’d never experience anything where we had healthy conversations and worked through things in a respectable way and it didn’t help that growing up, toxicity was a norm in my household, although I know my mom really worked hard to show me the “make ups” all I really witnessed were the fights and then them randomly faking being “ok”.

Now, it’s like I teeter between two lines.

When I don’t care about someone I have 0 tolerance for the drama. Absolutely not. Blocked. Never to speak to them again.

But if I do care about someone, it’s almost as if my brain equates drama to care and unfortunately a lot of us do.

I remember when I got into it with my FWB about a very very very touchy subject. I know for a fact we were both triggered and both could’ve handled the situation better but from what I recollect, he really did try to communicate gracefully with me while I… went the fuck off.

So here I am at 31 trying to figure out why I feel like there’s a little girl in me who just wants to be able to have fun and then there’s the other girl in me who wants to protect me from any and all harm.

It’s almost to say if XYZ happens again, it would be my fault because I didn’t see the signs.

That’s actually so mean and I don’t deserve self inflicted meanness.

The End Game: Have Fun

So I end this here to say that the current journey I’m on is trying to make sure every experience I have is drama free and FUN.

Yes, at the golden age of 31 I am learning how to have fun again. No one talks about how you have to relearn yourself and what you like as you age and unlike my 20’s, the new kind of fun I want to have won’t be reckless fun. It will be safe, conscious and thoughtful fun that aligns with who I am today and that’s SO damn exciting to me.

This requires a bit of a detox. I realized that I still have desires floating around in my head that no longer align with this current version of me but had been such a staple in my life in my 20’s that I THOUGHT they were still things I craved.

What’s interesting is, when I tried to think of some examples I couldn’t think of any but I think that’s because this is a newer revelation and honestly, I also need to reconfigure what DATING looks like in my head.

It’s completely okay for us to not know what the heck we want dating wise because honestly, it’s hard to know when the climate of dating is what it is right now but it IS important for us to do the work to begin our process of discovering what we want when we DO meet someone we feel aligned with.

My friends with benefits taught me this.

I think some important questions I need to reflect on are:

1. What do I TRULY crave right now?

2. If I met someone who was whole, healthy and ready to love, what would I desire from them?

3. What desires do I want to fulfill that will enhance the quality of my life?

4. Do I need a partner to fulfill these desires?

5. If my trauma hadn’t impacted my wants, what would I want right now?

And these questions may help you along your dating journey too.

Some desires don’t always require a detox but they do deserve a reconfiguration.

For instance, I thought I wanted to go to a movie theater to get fingered, which is very 18 year old of me and I actually still do BUT there’s a rule.

This can’t happen on my first date, this can’t even happen on the second, this is saved for someone who has already shown me how serious they are about my safety and care and want to take it up a notch in the spicy department. The yearning would be mutual and the crave for spontaneity and consensual fun would be the driving force.

This is NOT something I’d do with the person I just met who doesn’t want to invest in a hotel room, so they took me to the movies to get it on instead.

With that being said, I’d like for us to create a bingo card of fun.

Think of this as a bucket list but for exciting adventures that you can participate in yourself, with someone you just met or with someone you’re deeply getting to know.

This can include kissing someone in the rain, holding hands under a waterfall, going to see a play, getting dressed up as your alter ego, complimenting a stranger, the limits are endless and they can range from small to large in the spicy department.

The goal is to create a fun guideline to help you access your pleasure and put a name to your desires. Feel free to come up with many or maybe make one for date nights, one for solo adventures and one to explore with your partner.

Here’s an example of my fun bingo card which features a little bit of everything.

All in all my dears, this is just another way that you can explore your pleasure and what brings you joy.

I’m getting to the point of my dating experience (aka I’ve been on the apps for three weeks and am over it) where I think it may be more fun to have some external experiences. Experiences that can be contrived over an app were cool in 2020 but in 2026 it feels a bit more aligned to go out, feel peoples energies and get off the mary-go-round of people shopping via an app that feels like it’s a side baby of the dead internet theory.

I’ll keep you all posted on my podcast IADGAF and you can check out my PATREON to hear all about my latest dating adventures.

And if you want to learn about ALL of the ways you can invite more pleasure into your world then you are more than welcome to check out The Ethereal Pleasure Oasis pleasure portal and for a more curated experience you can check out my 5 week pleasure program created for beautiful, curious, embodied souls like YOU.

Xoxo

Love Atiya