It was a great date – until she opened her overnight bag

I wondered if maybe I was the problem; being judgemental isn’t my style (Picture: Annie F Bennett)

I woke up the morning after our date, groggy and blurry-eyed.

I turned over, saw she had left to go to work (as we’d discussed), and rolled out of bed. My feet hit the floor and abruptly stopped mid-step as – once again – I found myself face-to-face with Winnie the Pooh.

Rural Tennessee is not exactly teeming with romantic options for young lesbians. When I lived there in 2024, it was a very ‘get what you get and don’t get upset’ mindset on the dating apps.

But I was particularly excited about my date with Sam*.

We matched on Tinder and she seemed exceptionally normal – which isn’t always a guarantee – and when she showed up for our movie night date at my house with flowers, I was pretty sure we weren’t going for casual. 

After the movie ended, we kissed. ‘It’s getting late,’ I said. ‘Oh, yeah, we should probably get to bed,’ she responded. I took her by the hand and started to guide her towards my room when she stopped me. ‘Wait, let me grab my stuff’. She lived about an hour away, so I wasn’t surprised she had brought an overnight bag.

I tried to make a flirty joke: ‘Ooh, got any toys in there we can use?’

‘Yeah, actually! I can’t sleep without it,’ Sam said as she pulled out an early 2000s-era Winnie the Pooh teddy bear.

At first, I thought she was joking. 

We ended up making out but my mind kept drifting to that damn toy (Picture: Annie F Bennett)

What threw me off about the situation, besides the fact that I was face-to-face with someone’s childhood teddy bear, was the lack of embarrassment she introduced it with.

We all have embarrassing things to deal with – I’ve had to stop the flow of the evening to put my retainer in, for example – but usually when these things come up, they’re accompanied with a level of sheepishness which Sam did not demonstrate.

I wondered if maybe I was the problem; being judgemental isn’t my style. ‘I need to get over this,’ I thought.

So, I tried to get over it; I really did. We ended up making out but every time it started to go further, my mind drifted to that damn toy. I’d pull back my hands from sneaking under her clothes and slow the kissing down to a more PG-level of passion. Eventually, I accepted the unfortunate truth that I just wasn’t turned on anymore.

We fell asleep and she left the next morning.

Here’s the kicker: she left the teddy bear.

I was genuinely concerned. She lived an hour away and supposedly needed this bear so badly that she brought it on a first date just to sleep. So, I took a selfie in an attempt to be cute and sent it to her with the caption, ‘Forget something? ;)’ 

I took a selfie with the caption, ‘Forget something? ;)’ (Picture: Annie F Bennett)

A few hours later, she responded. ‘Oh my god, yes! Thank you.’

That was it. No plan to pick it up.

So, I said, ‘Of course! It’s a good excuse to see each other again. When are you thinking?’.

She didn’t respond. 

After another 24 hours, I finally got a text. ‘Sorry, I’ve been so busy. Please hold on to the bear.’

‘What?!’, I thought, indignant. ‘You were codependent enough to bring this to a first date but suddenly you’re in no rush to pick it up?’

Again, I asked when she wanted to come get it. Again, she did not respond.

I no longer believe in the ‘no strings attached’ hookup (Picture: Annie F Bennett)

That bear sat in my room for about six months.

Every once in a while, I’d text Sam about it and occasionally get some half-arsed response with no follow-through. At one point, I even checked it for hidden cameras.

Clearly, Sam did not need it to sleep every night; or even for half the year!

Every time I had sex throughout that period, I thought about this bear. It moved from my closet to my dresser to my windowsill, no place ever being quite right. I didn’t want to put it out of the room and risk losing it in case she suddenly decided she needed it back.

When, eventually, I found out I’d be moving, I sent one final text. ‘Hey. Honestly, this whole thing has been really weird. I don’t want to throw away your childhood teddy bear but I’m moving and don’t want to take it with me. Please send me an address I can mail it to if you’re not going to pick it up.’

I’ll never look at Winnie the Pooh in quite the same way again (Picture: Annie F Bennett)

Sam texted back with some story about work being busy and pretty much every go-to excuse other than the dog eating her homework – but she did, at least, give me her address. I was finally freed from the teddy bear as the post office took the package and thus broke me from my chains.

Afterwards, I started approaching sex a little differently. I no longer believe in the ‘no strings attached’ hookup. There is at least some level of intimacy that comes with opening yourself up to someone.

I can’t help wondering if Sam thinks of me and our exceedingly mediocre night together whenever she cuddles the bear that she probably once associated with scraped knees and pigtails. That bear made her my hilarious hookup story; but, to her, perhaps I’ve tainted some core aspect of her childhood without even meaning to.

But then again: I still don’t understand what went down there. How does someone rely on their teddy bear enough to bring it to a date but not need it enough to follow up for months?

I will probably never know – but I do know I’ll never look at Winnie the Pooh in quite the same way again.

*Name has been changed

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