My Boyfriend Was A High-School Bully. Is That A Red Flag?

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My Boyfriend Was A High-School Bully. Is That A Red Flag?

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Estimated reading time: 11 minutes

Hi Doc,

I’ve recently started dating a man we’ll call him “Jake” for privacy reasons. On paper, Jake seems perfect but there are a couple things about him that give me reservations about having a future with him.

Jake is something of a clean freak (he has a mental illness where he needs things to be a specific way otherwise he kinda freaks out) and he recently told me that he wouldn’t share food with/have food prepared by my best friend, because he sees him as an “unclean person.” Needless to say, that didn’t sit right with me. To the point that I almost broke up with him. I get that it’s a part of his mental illness, but for him to say that of someone he’s met twice just felt very judgy of him and I am so not like that. I am very much a “live and let live” kind of person.

Also (and this is one that I just can’t seem to get past), Jake has revealed to me that he was a “Mean Gay” in high school. Not like outward-bully kind of mean, like psychological-warfare kind of mean. Like if you cross him, he’s gonna make you hate your life. Again, I am so not like that. I’m all about love. Unless you’ve wronged me in some unforgivable way, I genuinely want what’s best for everyone around me and I’m very passionate when I care about someone (it’s the Aries in me).

These things make me hesitant about him, but then I think about how good he makes me feel and how everyone around me seems to think he’s perfect for me.

I’d love to know your take on all this

Sincerely

Hesitant in Love

Gotta love a Sir Mix-A-Lot letter, where everything is perfect… right up until you get to that big ol’ BUT.

I have to be honest, HIL, I think you may have your concerns somewhat backwards. I’d be less concerned about Jake’s behavior in high-school than his behavior now.

You don’t mention how old you and Jake are, but I’m guessing that high-school was a while ago for both of you. I tend to give people more slack about what they were like in high-school (to a degree) because, frankly, high-school is frequently more akin to the social dynamics of a high security wing of a prison than an educational facility. High-school is a time of confusion, transition and discovery, where a bunch of hormone-addled teenagers are starting to try to figure out just who the hell they are and establish an identity for themselves that’s separate from their parents’ ideas. It’s also a time of trying to process relationships, social hierarchies and the use of soft power, burgeoning sexual identities and oh, yeah, trying to work an education into this mix as well.

And when you throw in the teachers, coaches and now outside influences trying to censor books, shove kids back into the closet and generally turn everyone into little 50s themed automatons… well, it’s kind of amazing that everyone doesn’t come out requiring EMDR for all the trauma they go through.

A lot of folks in high-school were assholes. Some didn’t realize they were assholes. Some knew damn good and well what they were doing. But the common thing linking all of them is that those are the most chaotic years in a person’s development, physically, chemically, socially and emotionally. A lot of folks who were gargantuan bags of dicks in high-school often get over their bullshit in college or later – some through therapy, some through getting to a better environment and some just through the process of maturing and realizing how fucking awful they were. So I tend to see how someone was in high-school as more of a data point in their development, rather than something that defines and condemns them forevermore.

That’s not to say that the damage done in their wake wasn’t real or that it doesn’t linger… but it often can at least provide context.

But honestly? If you feel his being one of the Mean Ones in high-school is a deal breaker, then that’s legit. You get to decide what is or isn’t a deal breaker for you.

But honestly, that, in and of itself isn’t something I would necessarily say is reason to dump a guy. How people behave in the present tends to be more important to me. Someone who can acknowledge their past, take responsibility for their actions and try to do better going forward is generally someone who’s demonstrating growth and maturity.

This is why Jake’s past isn’t as concerning to me. His present on the other hand, suggests that maybe his past isn’t as past as it could be.

I’ve got a lot of sympathy for folks who deal with compulsive conditions or neurological and psychological issues that they can’t necessarily control. Having a phobia or a compulsive disorder can be hell for the person dealing with it. It’s rarely the cute “Detective Adrian Monk” fussiness so much as intrusive and disruptive thoughts that are relieved by certain actions or setting one’s life just so.

But having a mental illness or a condition doesn’t mean you can’t also be an asshole. Having a compulsive disorder or a phobia doesn’t mean that you don’t have agency or requires you to blurt out rude or mean things about people, nor is it a “get out of being an asshole free” card. So while I can sympathize with Jake having a need for a particular type of order and surgical levels of cleanliness to ease those intrusive thoughts, the fact that he felt free to say “hey, your friend is an unclean person” is kind of telling. And frankly, I have to raise an eyebrow at the language used. If those were his exact words – that they’re an “unclean person” – then my eyebrow’s in danger of shooting clear off my face. That’s… really loaded language, and it tends to go beyond someone being dirty or unsanitary.

So now I’m left wondering whether or not he actually has matured past being a “mean gay” or if it’s just the way that he behaves that’s changed.

So here’s a question for you, HIL: Is he just as judgey about, say, eating at restaurants? Or is he able to power past his reservations about cleanliness, even if he isn’t in the kitchen checking for their health department certification?

Have you ever seen Jake get angry? What about when he’s been thwarted or denied something he wanted? How does he behave when faced with minor inconveniences or setbacks? Or if he’s dealing with someone with less social power than he has in that moment?

For that matter, how does he talk about other people – people besides your friend? Does he talk about a lot of people he doesn’t like or finds objectionable? Are there a lot of folks that he finds to be “unclean”?

Is he free with his judgements about folks he barely knows or engages in a lot of shit talking about folks? Does he let his inner meanness come out at people who theoretically ‘deserve’ it? And if so, what did they do that made them deserving of his ire? Does he nurse a lot of petty grievances, or seem to be slighted a lot?

Absent some answers to these questions, I couldn’t say whether these are red flags or not, but I would say that it’s at least worth paying attention and proceeding with caution.

The last thing I’ll say: the fact that other people talk about how perfect he is for you shouldn’t be the determining factor in whether you stay or go. Relationships aren’t democracies or open forums. People can have opinion, but they don’t get a vote. Even if everyone swears up and down that he’s The One and you’re crazy for missing out on him, you’re the one who’s actually dating him. If his behavior is too sketchy for you or you don’t feel like you could date him because of how he was as a teenager, at the end of the day, that’s your call. No one else’s.

Good luck.


Hello Doctor NerdLove,

I need your advice, please. I’ve met a man at the religious outing (he is in his 50’s). Divorced 3 times but no kids. I was never married before. He had a heart attack twice as too much stress at work in USA (he relocated 8 months ago from USA to my city and bought an apartment here )

Also, working too much was a reason for his divorces. Can it be? We had a great, respectful date, and after that, we texted for a while. He said that he enjoyed our dinner date but he did not ask me out on a second date. I even told him that I like sports and want to be part of a club. He advised a place for me to try out, but there were no plans for us together.

Then, our communication stopped for 3 months. I decided to text him & ask how he was. He told me that he relocated to another country for work shortly after our date & found love of his life over there (his sister’s friend) who he’d met at her dinner party.

I was really surprised that he did not tell me anything before.

What would you tell him in my place? He told me before that he wants to stay here for good to enjoy life & now he is saying that he relocated to another country for work?

Did I scare him by saying that my fiancée passed away a few years ago (afraid that I won’t love again)?

Can you help me please to solve this mystery?

Warm regards,

Words We Couldn’t Say

There’s really not a mystery here, WWCS. In fact, pretty much everything about his behavior is pretty straightforward. You had a date, he said he had a nice time and that was it. He never proposed or even suggested a second date. He didn’t pick up on your hint of trying to find a sports club together or – more likely – did pick up on it and deliberately chose to ignore it.

And then he didn’t text you again for three months until you decided to try to blow the dust off the lines and see what he was up to.

Now, to be perfectly frank, this is all pretty clear, and you have to work really hard to think there’s anything to this besides his not being interested after the first date.

You don’t mention what country you’re in, but in the US, if someone likes you and wants another date, they’ll usually make that really clear. If nobody says anything or suggests another? Well, it’s possible that everyone’s waiting for someone else to make the first move, but the more reasonable assumption is that they’re not interested.

Case in point: the fact that he said he had a nice dinner with you was him being polite. The fact that he didn’t propose another date or say “I’d like to do it again soon” is the hint that no, there won’t be another date.

The same with not texting. That’s what we call “ghosting” – dude basically just decided that there wasn’t really a need to tie everything up in a bow for you, and so he just quit texting. Which, while not great, is par for the course. It might’ve been helpful for you if he’d said “thanks for dinner but I don’t feel a connection” or “I think we want different things, best of luck”, or something similar. But honestly? Y’all had a date. Singular. That’s not an oath sworn in blood or even a strongly-worded promise. He wasn’t interested in more.

Everything after that, was him being polite but distant. There’re reasons why you weren’t getting more than the most terse responses from him and why he let the texting go silent: he wasn’t interested in keeping it going. I have no idea if he’s telling the truth about having met the love of his life or even if he left the country. I suspect at least some of that was him giving you a softer “no, not interested” than he could have. His saying “I’ve met the love of my life” is, at least, a reason for you to let go of the hope of seeing him again. It may not be the truth, but it’s honest, in its way: there is no future for the two of you and it’s better for you to move on and find someone else.

Was he lying about wanting to stay? No clue. I rather doubt that anyone with a shred of emotional intelligence is going to say “no, I’m here because I have to be and I’d rather be anywhere else” to a local. It’s entirely possible that he was hoping to stay and got shuffled to another location. Or it’s possible that he saw a better opportunity elsewhere and moved on his own accord. Or, shit, maybe he’s still in the country, but somewhere else and thought it would be a cleaner break if you weren’t motivated to go looking for him.

Did you scare him off by telling him about your fiancée? No idea and, honestly, it’s more or less irrelevant. The same is true about whether he was or wasn’t telling the truth about wanting to stay. The only thing you really need to know is that he wasn’t interested in anything more.

There’s really nothing to say to him that’s either going to change his mind or make him regret ghosting you. Anything you do send or say is likely going to just vanish into the ether without a trace. The only thing you can really do here is pick yourself up, dust yourself off, chalk this up to someone just not being right for you and move forward.

There will be other people in the future. Just don’t start trying to plan a future with them until they’ve actually given you reason to do so. And that reason should be more than just one date with no follow up.

Good luck.

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