Friends with (My Kind of) Benefits

SO. I haven’t written in a while, and I apologize (to myself) but I will try and double back to share some “unconventional” dating stories in the next few posts.

I’m pretty sure I’ve managed to successfully hack sugar-daddy-dating system. Some how Lunch is totally fine with us being friends, platonic relationship all the way – no hand holding, no kisses on the cheek, no nothing. I clearly stated that was all I was capable of being with him, as he is married… and well, twice my age, but for the purpose of this argument we will stick with the former excuse. And guess what? He still wants to take me out for lunch, take me shopping, and has offered to continue to help me out financially when I need. I’m honestly confused and amazed and I’m not sure what’s in it for him. When I asked, his reply was equal parts sadness and sweetness:

“I’m lonely, and I enjoy seeing you.”

We met at the mall yesterday and he took me around to all of the different high end stores, bought me two new dresses, pair of shoes, purse, and a gorgeous raincoat that I would never in a million years be able to afford on my own (well on second thought, maybe at this rate…).

No price tag phased him which is still hard for me to wrap my head around. $1000 for a dress?

“Go ahead, try it on! If it fits, its yours.”

He paid cash for everything (he must carry around with him close to $5k in hundred dollar bills) and made it a point to give me all of the receipts. It didn’t occur to me why until my girlfriend pointed out that I can go back and return everything for cash. DUH.

I don’t think he cares if I keep the items or return them. He enjoys spending time with me, and it’s more fun to go around shopping than just eat together or take a walk. He wants to help me out financially but maybe it just feels nicer for him to buy me things instead of flat out handing me $500 or $1000 every time we meet. I get it. I like it. No complaints here!

Anyways, I’m still not totally sure how I feel about this whole thing. But it is feeling less and less weird, and I attribute that to my being completely forth coming regarding my intentions and limitations on our relationship. One thing I’ve learned – it is best, especially when navigating such a slippery slope, to be as straight forward as possible. I find the men appreciate it, it’s a breathe of fresh air for them, as they are used to women trying their best to manipulate and persuade them this way and that, telling them everything they think they want to hear. Not my style. And hey – It doesn’t always work out, but the ones who say sayanara after I drop my short and to the point “friend zone” speech, well, one less fella to worry about.

The best part about Lunch is how easy it is for us to just, hang out. Wether we are just getting lunch, or walking around a mall or anywhere else, he has never made me feel weird or uncomfortable, never walked too close or tried to put his hands on me, and our conversations flow. Obviously he is smart and successful and something of a socialite and it’s fun and entertaining (and dare I say educational??) to simply be around him.

And again, who knows how long this thing will last. I’m still waiting for the day he gets bored of me and starts looking for an actual “sugar baby.” But until then, I’m young, free, beautiful, and looking for some good stories to tell when it’s all said and done. And who am I kidding –  a Herve Leger bondage dress or two along the way wouldn’t hurt. 😉

-JAG

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