DEAR DR. NERDLOVE: I am a 20 year old student going into my second year at the University of Ottawa, and let’s just say that I have a bit of a troubled history when it comes to romantic relationships. I am very much a socially awkward and socially anxious person who has a fairly hard time working up the courage to talk to people and trying to find the right words to say in a conversation. This, combined with my difficulty understanding certain social cues and tendency to get obsessive about the people I have romantic interest in, can make it difficult to talk to the people I’m attracted to and to enter romantic relationships. Though it’s rather embarrassing to admit,  I have not been in one single relationship ever in my life, even though I’m 20 years old. Both of these problems (the social awkwardness and the tendency to get obsessive) impacted my first 2 semesters at Uni this year, which I will go into more detail below.

I have no idea why I had a crush on one of the girls who was in my psychology class during the 1st semester. We met at the global climate change protest march this past September. We travelled as a part of a residence group, but we didn’t hit it off or anything and we never talked to each other after the march. We were mere acquaintances at best and we didn’t seem to have that much in common. Nevertheless I developed this massive obsessive crush on her in the middle of October and I could not stop thinking about her until the end of the semester when I finally confessed my feelings to her via Instagram (she wasn’t interested and seemed a bit angry). It was really really bad and although I didn’t do anything inappropriate, I feel terrible because I creeped her out a lot. I probably should have slapped myself so I could wake up from my delusions and realise that she was not interested. To this day I am quite ashamed for how creepy I was during the 1st semester, because I don’t like or wish to make anyone feel unsafe in my presence. It was terrible and I’m trying my best to make sure that I don’t act that way again.

I really shot myself in the foot when it came to my relationship with a girl I was interested in the second semester. Unlike the person in the 1st semester, who I had a definite one sided crush on, this girl and I seemed to have a lot in common. At least in the beginning we seemed to have reciprocal feelings for each other. We were both involved in the board game club at school, we both like to read, we both enjoy biology, we both like visiting bookstores, and we both like listening to music outside of the mainstream. We had different upbringings as I was brought up halfway across the world in the suburbs of London, and she was brought up in the suburbs of Toronto. Other than that we had a fair bit in common. She had actually been quite friendly in the 1st semester as we shared an English class together and she talked to me in the residence, but it was only during 2nd semester when I joined the board game club and saw her at the Toronto bus station that we truly hit it off. We then went to a bookstore near the university although it was a disappointment when we found out that it was an academic only bookstore.

After the COVID-19 pandemic hit and everyone was sent home I really started missing her and I sent her messages on Instagram chat to try and talk to her. She got really annoyed with me and said that she didn’t want to talk to me anymore because I was invading her life and now I’m really convinced that I’ve shot myself in the foot because she was the first girl who ever openly expressed interest in me. To be honest with you I probably came across as a bit desperate when I was talking to her, which really turns women off.

Do you have any tips as to how to stop myself from obsessing over people and how to stop myself from shooting myself in the foot when it comes to potential relationships?

Thanks

TheLonelyBrit

DEAR THELONELYBRIT: Let’s start with the most obvious, TLB: you’re twenty. There’s nothing unusual or shameful about having not dated anyone yet. To be perfectly honest, I wouldn’t really regard most high-school relationships as being terribly significant. They get played up by pop culture, because the YA and teen audience has disposable income and time on their hands, but in the scheme of things, they’re ephemera. But part of the problem is that you’ve let yourself get twisted up by this supposed lack and I strongly suspect this is part of what’s driving you. It sounds to me like much of what’s going on is that you — like a lot of guys — are trying to make up for lost time.

Except the truth is that you haven’t lost anything, you haven’t “missed out” on anything and, frankly, there’s nothing especially magical or significant about relationships in your 20s that isn’t just as magical and significant about relationships in your 30s, 40s or onward. A lot of what people romanticize about young love is mostly limerence, new relationship energy and a hell of a lot of “I have no idea what I’m doing.” And as someone who has been there, done that and had more heartbreak than I care to think about (and even more shitty relationships) in my teens and 20s… honestly, people have a tendency to sand off the rough parts of what those relationships were actually like.

What I’m saying is that nostalgia is a hell of a drug.

Now the first issue you’re running into is that, frankly, you’re seriously over-investing in people. I mean, let’s look at your first crush. You literally knew nothing about her except that you found her attractive. That’s not the basis for… anything, really. Certainly not for making a huge confession about your feelings. I mean, on a strictly practical level, what’s there to be said besides “I think you’re pretty?”

However, I will give you this: sending a DM — singular — over Instagram isn’t the worst thing in the world. A little intrusive, a little presumptive and weird, but not intensely creepy or something to flagellate yourself over. Almost every female or femme-presenting friend I have gets randos in their DMs whenever they post pictures of themselves, and most of the time, they forget about it as soon as they delete the message. So I think you can let yourself off the hook for this one. It’s not a great look, but it’s not the sin that can never be forgiven. I’d say “just don’t do it again,” except… well, you did.

Your second crush is where you went overboard. Messaging a friend to talk is one thing. Messaging them over and over again, especially if they’re not responding, is intrusive and makes people uneasy. It’s a sign that you don’t have high emotional intelligence, or that you’ve started to fixate on someone in a way that makes them deeply uncomfortable. And while you know and I know that you didn’t mean any harm… your friend didn’t. And to be perfectly frank: I kind of suspect you were rounding up the amount of interest she might have had for you.

The second issue is the way you’re going about things. I am not a fan of “big confessions”, especially where romance and attraction are involved. While I get that those big, dramatic confessions make for great drama in shoujo manga and YA novels, in real life, they have a tendency to go over like a lead balloon. In a very real way, what you’re doing when you make a “confession” like that is that you’re dropping your feels in someone’s lap and asking them to do something about it. I’m a much bigger believer in being proactive and taking ownership and responsibility for your own feelings. So rather than confessing — whether in person, over text, a note or a DM — it’s better to ask someone out on a date. Not to “hang out some time”, not to “get together”, but a date. One that is very clearly a date. Not only is this more direct and active, but it also tells the person you’ve asked out that you’re interested in them in a non-platonic manner; folks very rarely ask someone they don’t like out on dates.

But  frankly, all of these are secondary issues. These aren’t the issue that you need to focus on. The overlaying problem — the one that’s at the core of all your other issues — is that you seem to have some form of emotional disregulation going on. It sounds like a lot of your life comes down to “you’re at a 10 and you need to be at a 2”, and it seems like you struggle with keeping things at a reasonable level. This might be a comorbidity with another issue, it could be a chemical imbalance, or possibly even a behavior you’ve over-learned over time. Now, as I’ve said many times before: Dr. NerdLove is not a real doctor, which is why I think the best thing you can do is talk to an actual mental health professional. Considering that this is a common occurrence for you, I think your first step should be finding a psychologist and talking with them about your issues. Considering that you’re currently a university student, you should take advantage of the resources your university has to offer; if there isn’t a counselor in the student health services, they can almost certainly provide you with a referral. And while I realize COVID can make it difficult to get in-person appointments, most therapists do assessment and sessions via telemedicine these days.

Talking to a psychologist will help you get a handle on what’s going on, give you some direction on how you can help manage your emotions more effectively and possibly recommend courses of treatment that’ll help get things under control. I’d suggest you start there; if you don’t treat the underlying causes, you’re not going to have much success dealing with the symptoms.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I need some advice. You’ve said before that, when asking someone out, no one gets to call dibs, just because another person dated them first doesn’t mean you can’t now, etc. The general gist of what I got from this is: the only people that matter are you and her, nobody else gets a say in whether you date her.

But what what about a sibling?

I’ve recently been spending some time with the sister of one of my good friends (I’ve known him for about 5 years, and just met her a couple months ago). And I think she’s pretty awesome. And she’s attractive. So, of course, I’d like to ask her out.

Obviously, if we were to start dating, we’d have to tell my friend. But, should I consult him first? How would I even begin that kind of conversation?

Any suggestions you can give me on this would be awesome. Thanks.

– Bro Fist

DEAR BRO FIST: Dating is not a democracy. Unless you’re already in a relationship (in which case, different rules apply entirely) other people don’t get a say in your dating life. Period. They are allowed an opinion – and most of the time would do well to keep it to themselves – but not a vote or a veto. End of.

Now, this doesn’t mean that dating is consequence free as a result. When you’re dating a friend’s ex – or in your case, a friend’s sibling – then things can get complicated. There IS the possibility for hurt or complicated feelings, and that CAN put a strain on your friendship. These are some of the risks you take, and you have to be willing to do the math and decide if these risks are acceptable to you.

Are you obligated to consult him first? No, not really. This is the 21st century; his sister isn’t his property and she’s free to date whomever she damn well pleases, whether he likes it or not. You hardly need his permission.

(Hell, I don’t even like the idea of asking a woman’s father for his blessing to propose to his daughter. Giving a heads up? Sure. Asking permission or for their blessing? Not as much.)

All that being said, your buddy may well not be cool with your dating his sister for any number of reasons. Presumably he knows you better than anyone else; if he knows you’re a horndog, he’s not going to appreciate the idea that you’re trying to work your way into her pants – never mind that she’s capable of making her own decisions. He may worry that you’re going to hurt her or that she may hurt you. Or he may think it’s cool, he may think that she’s a grown-ass woman who can handle her own affairs, or he may not give a damn one way or the other.

Thing is though: his opinion on the matter is your secondary concern. You should ask her out before you worry about what he thinks. No point in getting all worked up if li’l sis turns you down flat.

Do you NEED to consult him? No, not really. Should you give him a head’s up? Yeah, it’s good manners and you don’t want to seem as though you’re sneaking around behind his back; that’s a great way to destroy a friendship and possibly catch an ass-beating in the process.

I’m not saying that it won’t be a tricky situation; some brothers are extremely protective of their siblings, especially if they’re younger. Pull him aside and tell him him that hey, you and his sister are really starting to hit it off and it seems like the two of you might have something good going and you wanted to let him know because you’re his friend and you respect and care about him. Be straight with him, be respectful… and for the love of GOD don’t make any sort of even vaguely sexual jokes about her. Again: great way to catch an ass-beating.

Good luck.

DEAR DR. NERDLOVE: Long time reader, first time writer. My question is simple, yet I think I would benefit from some of your insight.

I’m a guy who started taking singing lessons a few months ago, just to expand my musical repertoire. I was surprised to see that all the other students are girls roughly my age (early-to-mid twenties), and with similar interests. Just to quickly clarify, the lessons themselves are private, one hour sessions, with the same teacher. This means that by the time one of us is done and leaving, the other is just arriving. I guess you can see where I’m going with this.

Long story short, I would like to ask one particular girl out who is scheduled right after me. Just a quick coffee date to get a chance to know her better, since she’s incredibly cute and I know for a fact that, aside from singing, she also plays bass which is just awesome on so many levels. The problem is that there’s really no appropriate time, or way, for me to do this. 

The only time I have to talk to her is when I’m leaving and she’s arriving, which not only is usually less than a minute, but is also incredibly inconvenient, considering we’re all on a tight schedule and asking her right before a lesson would put her in a position where she has to answer real fast, and in front of our teacher. It would feel less like an actual “move”, and more like  a cheap trick to pressure her into saying yes as quickly as possible. 

I could ask her number from said teacher (who has our contact information), and ask her out that way, but there’s no way to do that and come off as anything, but a giant creep whose only in it looking for some tail. It feels rude and spineless, and frankly I’d rather do it in person. 

The best option I could come up with was to finish my lesson, go into the nearby café that’s literally 10ft away, order a cup of tea (earl grey, hot), wait an hour, and ask her after she finished. While I can see this as something “cute” and safe, since she’s no longer pressed for time, or in an “official” environment, I also realize the stalker aspect in such a move. I guess I could say that I “just happened” to have had some business around  there, but I’ve always found these “fabricated meet-cutes” to be dishonest and cowardly.

So my question is, do you think it’s acceptable to “camp out”, so that you may talk to someone at a more appropriate time, and if no, I would greatly appreciate some advice.

Cautious Approach  

DEAR CAUTIOUS APPROACH: Sweet Zombie Jeebus, CA, don’t camp out and ambush her. That’s a great way to come across like a creeper even when your intentions are entirely aboveboard and honorable.

While we’re at it: trying to get her info from your teacher? Lean in a little closer, I want to make sure you get this:

NO! NO! NO! NO! NO! NO!

And also: NO!!

F--k me running, it’s a good thing your instincts are telling you that’s a bad idea. Yes, trying to weasel her info out of her teacher is pretty spineless. It’s also even bigger stalker behavior, potentially illegal and a huge violation of your crush’s privacy — and that’s before we even get to the part where you’re trying to convince a bystander to betray her trust in him. And what the hell are you going to say to her when you call her out of the goddamn motherf--king clear blue sky? “Hey, remember me, you have voice lessons right after me. How’d I get your number? Hey don’t worry about it, it’s no big deal so are you doing anything tomorrow? Hello?”

If you’re really lucky, you’ll only have ONE restraining order to deal with.

The best thing you can do is ask her yourself, in person, when you see her. It doesn’t have to be high-pressure at all. Leave a little early, so you can catch her before she comes into the room – that way it won’t feel like an ambush, more of an idea in passing. Relax, give her a friendly smile and say “Hey, you know what? We see each other almost every day and I barely know anything about you, but you seem like you’re really cool. If you’re interested, I’d love to buy you a cup of tea after class and talk music.” Short, simple, to the point. If she’s down, tell her you’ll meet her at the cafe. If not, then you shrug, smile and say “Ok, cool. Have a good lesson!” and roll on like all she said was “yeah, I think it’s going to rain this weekend.”  Next time you see her, it’s business as usual. You can do your “Mornin’ Sam / Mornin’ Ralph” routine as normal.

If you don’t treat it like it’s a big deal, she won’t treat it like it’s a big deal. You’re asking her to meet up for tea and friendly talk, not to bear your children.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: Let me get straight to the point: how do we feel about snooping through our significant other’s phones?

Unfortunately I did it, twice & saw her telling a very close friend that “she’s single forever”, even after dating for about two months. We are pretty serious, or so I thought, what with having met each other’s parents, introduced to close friends and sleeping over at each other’s places.

The second time I did it, (Yes I’m ashamed but when you get curious what are you to do?) it was texts between her and her ex. He mentioned a very cool date I took her on and then said “he’s a keeper” and once again she said she will “remain single forever.” After a couple more texts, SHE invited him out for drinks, which is very disrespectful.

In my eyes, I have done nothing wrong and have been the best man I know how to be to her, her family and friends all like me and the same with mine but I’m not dating them, I’m dating her. Is this a sign of what’s to come already?

I’m not proud of myself for what I did but now I found all of this out and I’m just not sure how to bring it up, what to do, etc. This is my first real relationship in a very long time, I have no problem getting women but when I love, I love hard.

Snoopy McPrysALot

DEAR SNOOPY MCPRYSALOT: Hoo boy, Snoopy, when you f--k up, you don’t do it small, do you?

Yes, this is a sign of what’s to come… it’s a sign that you’re going to get dumped because you can’t trust your girlfriend. 

So let’s talk about what you did. You snooped. Snooping is bad. Period, end of story. It only becomes “justified” retroactively if and when you find proof of wrongdoing, which still doesn’t mitigate the initial sin and only complicates matters and almost inevitably derails the conversation as to who’s wrong was greater.

And, the funny thing about when you snoop: you tend to find things out that you didn’t want to. Sometimes you find evidence that somebody’s doing you wrong. Other times, you find things that will just make you upset and uncomfortable and you’ll wish you didn’t know and won’t be able to bury it deep enough to forget that you found out.

And then there’re the things that can seem incriminating without context. And now you can’t have a conversation with her about it without revealing your sin as well. Good luck with that conversation, because there’s pretty much no way this is going to go well for you.

So let’s talk about what you’ve learned. First: she doesn’t consider you two to be in a relationship. While this isn’t something you wanted to see, this is also not entirely unreasonable; unless the two of you have had the defining the relationship talk, you can’t reasonably make assumptions that you’re on the same page about where things are going. Even passing certain relationship milestones doesn’t necessarily mean anything. For many couples, meeting the parents doesn’t necessarily mean anything other than timing. And considering what you read… it’s pretty damn clear that you aren’t on the same page.

Then there’s the fact that she’s still talking with her ex. Yes, and? The fact that they’re broken up doesn’t necessarily mean that they’re never going to talk again, nor does going out for drinks mean that something untoward is going on. Shocking I realize, but people can be friends with their exes after they break up, even go out for drinks on occasion. Unless you were finding some serious sexting going on, I suspect the problem isn’t with her, it’s with her snooping would-be boyfriend… and just in case you’re unclear, I mean you.

So let’s be frank here: no you’re not being the best man you could be, nor are you in the right here and yes you did do something wrong. You’ve violated her trust twice now. You didn’t even do it while looking for evidence to confirm your suspicions (not that this makes it better) but because – in your own words – you were curious. There really aren’t good reasons to violate the trust of someone you care for, but doing it just because you’re curious is especially s--tty.

No, you don’t have anything to say to her because, frankly, a) she hasn’t done anything wrong and b) you violated her privacy in a pretty heinous way

What do you do when temptation strikes and her unsecured phone is within reach? Here’s what you do: you sit on your motherf--king hands until the urge goes away. Either you trust your girlfriend or you don’t. If you do, then you shouldn’t be going through her phone. If you don’t, then you still shouldn’t be going through her phone. If you don’t trust her and think the best way to confirm things is to violate her privacy, then just do yourself the favor of breaking up with her. If there’s no trust, then the relationship isn’t going to last anyway and ending it sooner rather than later is just a mercy-killing.

So next time, check in with your girlfriend and find out where you both think you are before just assuming you’re both serious. And encourage them to password protect their phones if you can’t control yourself.

DEAR DR. NERDLOVE: There’s this guy I really like, and, well it’s hard to tell if he likes me or not. He’s just a really nice guy; he always says yes whenever I want to hang out with him, he’s always there for me (he even said so himself), he compliments me like “You’re cool,” or “Awesome,” but never like “You’re pretty…”

And then he calls me bro and stuff.

He replies with long paragraphs but takes forever to reply. We’ve talked on the phone for hours once. Whenever we hang out alone he likes to stare at me; it’s like he stares right into my eyes. He always gets really close to me but doesn’t touch me or anything. I’m always asking “what, are you cold?” but he never says anything. He doesn’t mind paying for me if we go out; even when I tell him I have money, he insists. He’s such a gentleman too.

The problem is he’s my ex’s friend. They’ve known each other since they were younger. My ex gets jealous when we hang out but my crush/friend says he shouldn’t care anymore and says it’s sad that my ex doesn’t trust him or whatever. So I’m not sure if he’s shy to make the first move or if he’s scared of what my ex will think or if he just likes me as a friend I just don’t know what to do.

Bewitched, Bewildered and Bemused

DEAR BEWITCHED, BEWILDERED AND BEMUSED: There’s a pretty simple solution to this B3: you should make the first move. It’s pretty clear that your crush is interested in you, but he’s holding back. Why? Well, probably because he has no idea how you feel. You and he (and your ex) all sound pretty young and the less social experience you may have, the more hesitant you may be to court rejection. So from the sound of it, he’s pulling the move from Hitch: moving in 90% and waiting for you to move the remaining 10%.

It’s also entirely possible that he’s afraid of pissing his off his bro by asking you out. But, the fact of the matter is, you can’t call dibs on someone. The fact that you used to date his best friend doesn’t mean that you’re forever off-limits to the rest of his social circle. It’s on your ex to get past HIS issues, not to try to regulate your social life for the rest of time.

Regardless, you’re in stasis here and nothing’s going to change until someone makes a move. Since your crush seems paralyzed, you might as well be the one to do so. So find a moment and either use your words to ask if he’s interested in dating, or initiate a kiss. The worst case scenario: he says no, you both have a moment of awkward laughter, then move forward. Best case scenario: you and your beau finally enjoy that electric first kiss.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com