Trigger Warning: Friend Cuddle Follow-up

Please do not read if you are not in a good place. The last thing I want to do is ruin anyone’s day when everyone has been so supportive of me here over the years.

Trigger warning. Sorry!!

A few weeks ago I had posted about an old college friend of mine (let’s call her Emily, not her real name) and I talking about having a cuddle session as friends.

She lives in Brooklyn and I’m out in the middle of Notown, Nowhere (population: me).

I went out to see her this past weekend. Flew into JFK, stayed in a midtown hotel. Surprisingly TSA wasn’t too long of a wait, at least coming from a smaller airport going to JFK. I gave myself tons of extra time because I did not want to miss seeing Emily for anything.

We had agreed she would come out to see me in the lobby of my hotel (hence “her coming to see me”) and go out to dinner.

We planned to meet up at 6pm but when I didn’t see her at 6:30 I started to worry and have all sorts of crazy thoughts like something bad happened or maybe she just forgot.

From the lobby just after 6:40 i saw her come into the main entrance looking around, scanning people. I saw her before she saw me.

God she was as beautiful as I remembered, really seemed like no time had passed.

When she saw me she yelled “Toadie!” ran up and gave me a big hug. I don’t read too much into that because she’s a hugger and hugs all her friends, women and men.

It felt surreal seeing her again after so long. We kind of did the catch up small talk about my flight, her work, my work, and the city. Honestly it was a little bit awkward, maybe I had built it up so much in my head and rehearsed it so much the weeks before.

We went to a sushi restaurant close by that was pretty upscale but not crazy expensive.

One thing that shocked me was how well she was dressed, makeup, trace of perfume, beautiful outfit with cleavage, high heels (which kind of is rough on 5’2” me).

She also had a carry on luggage she was pulling and asked if she could leave it in my room, of course I said yes.

Dinner conversation felt more natural and less forced than hotel lobby catch up. She opened up, said she had not been seeing anyone since her breakup with Tom and she didn’t really have any true friends in NY, only some women she would occasionally get a bite to eat with and do happy hour after work. Another thing that surprised me in a good way: she sat NEXT to me instead of ACROSS from me.

I totally honored her statement of “cuddle session as a friend” but during dinner a few times she placed her hand on my thigh and held long gazes, and at one point when we were talking about a mutual classmate/friend … him and his wife just had a baby girl, Emily looked me in the eyes and said (with hand on my leg), “I bet you’ll make a great Dad someday.”

I wanted to not be a creeper or violate her trust so I didn’t make any moves on her but I also did not push her hands away or anything.

She offered to treat for dinner since she said I’m a visitor but I insisted on paying. We went and hung out at Central Park a bit and did the horse drawn carriage ride. I insisted on paying for things even though she offered, since I really felt like she was trying to help a friend (me) going through a rough patch.

The entire outing she either held my hand or put both her hands in my elbow which was shocking since despite being close friends we never held hands in college. Heck, that was the first time I held a girls hand, even as a friend so it felt weird and wonderful all at once. Honestly it felt like a “couple thing” but I didn’t say anything for fear of upsetting her or spoiling it.

She kept telling me about how much she missed me and our times together in university and how good it was to be together in person again.

We laughed about old times like when she signed up for “assassin game” in our dorm lobby, didn’t know exactly what it meant, forgot about it, and turned the corner leaving Chem class with me and had Kevin spray her in the face with a water gun while I stood like an idiot with my mouth open and yelled at him “dude the hell are you doing?!”

Emily was actually the one who said “still down for cuddle session at your hotel?”

We went back and she asked me if i could stay in the lobby and let her use the whole room to get ready. Said she would text me.

That was the most tense, excited, emotional wait, I just paced around the lobby and tried to work off the nerves.

Took over a half hour (not complaining) but my phone buzzed and I saw her text just one word: “ready“.

Going up the elevator and down the hall to my room felt like an out of body experience like watching someone else.

When I went into the room she was tucked under the blanket except her head. She asked if the door was closed, and when I said yeah she asked me to go and double check, which I did.

when I came back she had tossed off the comforter and blanket and my god I hold that instant mental snapshot in time forever and replayed it in my head like a thousand times this past week. She was wearing see-through black lingerie top, completely see through which exposed her breasts and lacy red underwear. I feel weird trying to narrate it, and seems unreal as I write it but it really happened. I guess I knew such outfits existed but I never imagined I’d see a real life woman wearing something like that and especially never imagined it being for me.

I was just too shocked to say a word or move. The good thing is how well she knows me, she made it easy. She said “I’m wearing almost nothing, you should too. take everything off and come over. Or if this isn’t what you want I understand, if that’s the case look me in the eye and tell me this isn’t what you want.”

It would have been harder/more awkward to say no and being with her was what I wanted more than anything so thankfully there really wasn’t a way for me to screw up without tons of effort. I just took everything off and got into bed like she asked. :-)

i don’t want to go into too much more detail other than we did not “go all the way”. She was great with communication and drawing boundaries. Right when I got into bed she stopped me, looked me in the eye and said “you can touch me anywhere but not inside my underwear ok?” she “wasn’t ready for me to touch her inside her underwear yet”. She’s also so self-assured and patient.

Again not over sharing but honestly it was the greatest day/night of my entire life and changed everything.

Next 2 days were spent sightseeing. Empire state building, the Met, more time at Central Park.

We talked a lot, some meaningful, some BS, some just commentary about the sights around us. One important thing we talked about was her therapist. She told me everything/ After her breakup with Tom (that asshat threw her iPhone in a pond at one point) she and her therapist had a session where the therapist asked her, “Emily, what about Toadie?” She had told her therapist about me during their sessions over the years, and that I was like a brother for her to confide in and a shoulder to cry on and she considered me one of her best friends since university, well over a decade ago.

Apparently her therapist had her do a thought exercise: “what if in 5 years you’re still repeating the same self destructive pattern of dating, you call Toadie for a shoulder to cry on and he‘s a lot more distant because he’s married with a baby at home and his wife didn’t want him talking to you?”

Emily told her therapist she would be happy for me, sad for herself, and truthfully regretful and jealous.

Her therapist suggested she consider breaking her toxic cycle of dating and just give what she said some thought. I guess that’s what got the ball rolling and she bounced it off some of her closest girlfriends. She said Kim (not her real name, one of her bff from college, part of our friend group, I also consider Kim a friend though not as insanely close as the 2 of them) said it was a great idea, and told Emily “if you break Toadie‘s heart I’ll never speak to you again.”

Kim also told her “you know if you do sleep with him he’s gonna propose to you within a week!” So Emily made me promise not to do something impulsive like that.

Emily also admitted that she framed it as a “cuddle session as a friend” just in case things felt wrong or off, that way she had an out, and it was a game day decision, her attire and approach for the evening.

So I will admit, I somewhat think she’s ”settling”, or maybe she really is weary and tired of the highs and lows of dating the tall handsome dude she met while clubbing who grabs her phone and throws it in a pond during an unhinged bout of anger during a fight. Had a lot of time to think about it.

The whole time we were sightseeing Saturday and Sunday she held my hand or slipped her hands in my elbow.

Flying out of JFK back home Monday was pure agony, not because of TSA wait times but because I wanted to live in the moment forever.

Lol I’m already trying to work with her to figure out when I can go back out to see her again even though I’ve only been back home a few days. It all still feels unreal, this sort of thing just does not happen to me. I’ve seen it happen to friends though so I knew romantic relationships existed, I had figured since it hadn’t happened in well over 3 decades of living it never could.

We are talking nightly on FaceTime. We don’t have a “status”. She did promise she would not see anyone else and I responded by promising the same (really funny because we both know my “other prospects” are zero). I asked her if I could call her my girlfriend and she said I could call her whatever I wanted, she didn’t care about labels.

Not gonna lie that was a little disappointing/hurt, maybe she’s ashamed of settling or dropping her standards. However I do have hope now, for possibly a better future.