Dating the Best Friend

A

Anonymous

Anonymous

I don't think my best friend or anyone in our circle is on here, but on the off chance they are, I'm making this post anonymous and gender neutral, just in case. My past posts and writing style will probably give me away, but still, precautions are precautions.

So, I've known my best friend for nearly a decade now. They reached out to me once when I went through a hard time. Since then, we've had each others backs more times than I can count. We've done road trips together. Long, late night conversations. We're both creative people and we've bounced ideas back and forth on our latest hairbrained schemes. They've said I give far better, constructive feedback than anyone else.

When we first met, we were both with someone (I admitted to them I had a small crush on them when we first met). I've been single off and on since then, but they've always had the same partner. They've introduced me to a number of their friends; some led to short dating, one to a short relationship.

Their partner was...not exactly perfect. They weren't abusive, but they had a sarcastic, passive aggressive way of dealing with my friend. I've often wondered if it was borderline emotional abuse or manipulation. Little sarcastic jabs, not being emotionally supportive or distant, especially when it came to my best friend's ongoing mental health struggles. That's something my friend and I always had in common and been there for each other.

Now, I never wanted to get in between the two of them because despite the troubles, they made a good, cute couple. And I was more than happy to have a great friend who really got me. Their partner claimed not to be jealous of our friendship, but I sometimes question that because of the comments they'd make. Like if we went to see a movie without them, they'd make a snide joke about our "date." And I believe there was some snide comments about my friend cheating on them with me. It never really bothered either of us too much because they were, seemingly, superficial jokes. There was never an outright, serious accusation. Their partner worked odd hours and often missed out on joining us to see the latest movie. If they were available, they were ALWAYS welcome to join along. I didn't know their partner terribly well, or spoke to them much one-on-one, but I knew them well enough to call them a friend, at least. But there have been times that we've gone out, just the two of us, to movies or trivia nights or road trip excursions, and a few times people confused us for being a couple.

Anyway, my best friend and their partner broke up about two months ago. Best friend was an absolute wreck, as anyone expected they would be if it ever happened. Their partner dumped them unceremoniously and moved out that same day. My friend is slowly getting to a better place now, more focused but stressed out over their job than anything else these days. And we've been talking and hanging out a bit more lately.

To give them a safe space, away from their place that reminds them too much of their partner, I gave them spare keys to my place. They haven't really taken advantage of it yet, but the option is there. They stayed the night this past weekend. Nothing happened, mind you. I had an air mattress so they slept on that. We just hung out, talked, watched a movie, etc. As far as I can tell, there was no spark or hint of intimacy. But it was nice. It was comfortable. They even pointed out they hadn't once felt the need to smoke their weed - usually used in times of high anxiety - because they felt so comfortable here. There's a particular video game they love playing to destress, so I've had that downloaded in case they wanted to play it. And they did, which they said made them feel even more comfortable.

And I guess...after our long history, of spending so much time together, of knowing each other so well, I guess the question constantly in the back of my mind is...should we? Should we try dating?

To be honest, I'm not sure if I'm asking this looking for actual advice or if I'm asking it myself, almost rhetorically. I've said to myself before that I love them, absolutely, but I'm not sure if I'm IN love with them. Neither of us are exactly our usual respective "type" that we're into. And I also want to be mindful of the feelings of her friend I had a relationship with, not just because they're still really good friends, but because I think their friend still harbors feelings for me. Our breakup was mutual, though we've had the odd casual sex since then (not in years, though), and we've remain relatively good friends. But I feel like that added scenario might make things...awkward.

And of course, there's the potential of losing a best friend out of this if things don't work out.

I guess this is one of those things were I can't help thinking to myself, "Why not?" We like each other. We enjoy each others company immensely. We know each other pretty well. Maybe a dumb example, but I think about in Spectacular Spider-Man, where he has some great news and the first person he wants to tell is Gwen, and he realized how much he cares for her right there. That's similar with my best friend. The first person I want to tell ANYTHING, good or bad, is them. I often hold off posting something on social media so they can be the first to know.

On the other hand, I don't know if similar feelings are on their mind. They're still raw from the break-up, which is understandable. I don't want to be just a glorified rebound, nor take advantage of how vulnerable they're feeling. I sure as hell will NEVER make the first move or even make a hint of a move without them clearly consenting or giving a sign. Even then, I wouldn't want to misinterpret a "sign" and push something they don't want. No, if something were to happen, they would have to make the first, blatantly clear move.

If it doesn't happen? I'm okay with that. I still get to have my best friend to confide in. If they find someone else, I'd be happy for them.
 
I don't really have any advice for you. I'm just posting because your profile picture was turning up in the "latest posts" sidebar under this even though you posted as anonymous.
 
should we? Should we try dating?
I don't think so. Not at first, at least. Not until the rebound is good and done.
Continue to be a valued friend, continue to offer help and refuge, but you've already said that "...Neither of us are exactly our usual respective 'type' that we're into."
So be a friend, benefits or no, but be a friend. If it grows into something more later, then so be it, but it should probably be something that "happens" as opposed to something you both "try." I don't know enough about either of you to know how "try" would work out, but I am going on the many experiences of (myself/others) that suggest it is not easy for a friendship to survive a brief flare into a relationship. It is possible, just very much not common, because it requires both parties to accept/anticipate and be prepared for an eventual return to friendship prior to the "try."

-Patrick
 
I don't have great advice because just by the nature of this type of posting I can't know all the ins and outs of your life and all the context.

But from what you've written it remind me of one of the reasons I love my wife. I can be kinda boring around her because we're just comfortable with each other. I can be vulnerable around her because I know she's not going to judge me or hurt me.

It kind of, from my limited perspective, sounds like that's where you two are having essentially skipped the first few years of dating.

The only real thing I take issue with is this other friend who may have feelings for you? Don't worry about that. That's not something you can control and it's not healthy to shoulder the burden of regulating someone else's feelings or behavior.
 
I would advise giving them time to grieve their relationship and to recover from it before taking the next step.

Right now it sounds like they really need a friend.

Down the road? Based on what you’ve written here, it’s worth exploring for sure.
 
I'm going to jump in with some first hand experience dating a friend. Not my "best friend" per se, but definitely a friend.

It went horribly. As soon as we started trying to have a relationship, she turned controling and manipulative. We lasted about a month give or take and I have not spoken to her since. We were great friends at the start, but I lost her. I still think about her on occasion and hope she's doing well, but would never reach out to her.

Now, that was my experience. It sounds like you have a much stronger bond already than we did. So will you be the same? Probably not. My friend turned into a completely different person after we started dating. I hope you know your friend a lot better than I apparently knew mine. Just be aware that if things go badly, it could mean you never see them again.

A lot of what you describe sounds like a long-term relationship anyway. As @phil said above, it reminds me of how my spouse and I interact. Dill came over to my house for a weekend and was so much more comfortable with me than living with their sister that they never left.

So my advice, as others have said as well, is to give it time. Don't push it. Just let things go along and if it continues as is, with neither of you veering off path, broach the subject then. Or maybe they will.

Best of luck to you both.
 
No point being anonymous now, since I showed this post to her.

So...things may have happened.

She came over last night, with a dog she was dog-sitting. She actually wanted to come over to get incredibly drunk because she never really had before. She specifically said she wanted to "cut loose." So I joined her in the drinking, though I drank a bit more responsibly (taking it a glass at a time; she chugged from the bottle a few times). And she got...pretty wasted. Like, flopping around so much that I had to rescue her from my tub when she fell in after using the bathroom. Half the time, I was just making sure she didn't hurt herself.

Well, at one point, while we watched a movie, she drunkenly flopped towards me, collapsed on my lap, and fell asleep right on the spot. I tried to figure out a way to escape from under her so I could maybe get a blanket and pillow for her. She woke up after about 30 minutes and we talked...and cuddled. Something we'd never really done before. A few times, she tried going in for a kiss, but I reneged because she was still very drunk and I didn't want to take advantage of her. We talked a lot, I told her how I felt, and it turns out she's felt the same way for a long time (possibly even while she was with her partner). And we kept cuddling, talking about everything.

She started sobering up and we took the dog for a walk...where we had our first kiss.

We went back inside, talked more, cuddled more, kissed a little bit, but nothing more. I was adamant that if we did anything more, then I wanted her fully sober.

Today, we just spend all our time together with this new intimacy. I had to repeat a lot of the things I told her last night because she only remembered snippets. And it's so strange just how quickly we fell into being so comfortable, cuddling and being intimate. Got a bit hot and heavy at times, but we didn't go any further, despite being really tempted.

Sooooooooo...yeah, things happened and I don't know what to expect next, but both of our cheeks hurt by the end of today from smiling so much.
 
You couldn’t waterboard me enough to get me to tell my wife that this place exists. If she saw me on this site and asked what it was, I’d lie and say I’m setting up dates with other women.
Back when I was new with my ex-wife, she was here. But she got bored soon enough and quit visiting as often, because our niche nerd culture wasn't super interesting to her.
 
My ex found out about it, and while it didn’t cause any fights, I could not explain what this place is in a way that didn’t sound horribly embarassing.

“Ok, well you see, back when I was 13, I liked this web comic PvP…”

“Ok well a webcomic is a comic that is only on the internet.”

“Ok, well PvP is short for Player vs Player. It was a term commonly used in MMOs.

“Ok well MMO is short for MMORPG which stands for…”
 
My ex found out about it, and while it didn’t cause any fights, I could not explain what this place is in a way that didn’t sound horribly embarassing.

“Ok, well you see, back when I was 13, I liked this web comic PvP…”

“Ok well a webcomic is a comic that is only on the internet.”

“Ok, well PvP is short for Player vs Player. It was a term commonly used in MMOs.

“Ok well MMO is short for MMORPG which stands for…”
"It's a forum full of people I've known a long time"

What's embarrassing about that? Some of my best friends to this day are people I met on the official Diablo strategy forum
 
"It's a forum full of people I've known a long time"

What's embarrassing about that? Some of my best friends to this day are people I met on the official Diablo strategy forum
“it’s a place with this one dude who feels the need to explain why jokes aren’t logical”

“ok lots of people.”

“ok including me.”
 

Dave

Staff member
My wife has met a few people from here and she was surprised they were “normal “. She’s aware and supportive (I’ve spent a lot of time & money here) but she’s a Facebook kind of girl, not a forum kind of girl.
 
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