life

Is It OK to Date Your Best Friend’s Sister?

Ask Dr. Nerdlove by by Harris O'Malley
by Harris O'Malley
Ask Dr. Nerdlove | September 22nd, 2020

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

Love & DatingEtiquette & Ethics
life

Is It Ever Ok To Snoop?

Ask Dr. Nerdlove by by Harris O'Malley
by Harris O'Malley
Ask Dr. Nerdlove | September 21st, 2020

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

Love & DatingEtiquette & Ethics
life

Why Won’t My Husband Buy Me Flowers?

Ask Dr. Nerdlove by by Harris O'Malley
by Harris O'Malley
Ask Dr. Nerdlove | September 18th, 2020

DEAR DR. NERDLOVE: I’m a mid-30s cis woman who is happily married to a mid-30s cis man.

When we got married two years ago — and when I was still in the swooning stage — I asked my husband if he could surprise me with flowers sometime. This is an unusual request for me because I’m not usually the cutesy or flowery type, but perhaps I’ve seen one too many rom-coms. I just thought it sounded sweet, and my husband said he would do it sometime.

Now we’re about to enter our third year of marriage and I’ve still never gotten flowers. I bring it up occasionally (and I do mean only every few months at the most, not nagging!) and he always says that he just never thinks about doing anything like that.

For the record, I have gotten him lots of things over the years to show my affection — a new case for his electronic equipment, a video game he had been wanting, new tools, etc. He loved all of this stuff, but he’s never reciprocated.

I have to admit — like a stupid schoolgirl — I get my hopes up a little every Valentine’s Day or whenever my birthday rolls around, but nada. We’ve had discussions about romance or ways to keep our affections alive, but he usually says that’s “not his thing.” Last time I brought up the flowers, I said I wanted to feel surprised by them just once in my life — and I literally mean once will do — but he got annoyed and said he showed his love when he married me and doesn’t need to do it every day. I suppose he has a point and maybe I’m asking too much.

On one hand, I feel like a fool of the utmost proportions. With everything that’s going on in the world, I’m worried about some stupid flowers?! And yet, that also makes me angry. For goodness sake, it’s one bouquet of damn flowers. That’s all I’ve ever asked for and somehow that’s too much for him.

I’d be lying, Doc, if I said I wasn’t spiraling into resentment here. And for what? I don’t know.

I suppose I just needed to get this off my chest. I guess I’ll just buy myself some flowers and be done with it.

I Never Promised You A Rose Garden

DEAR I NEVER PROMISED YOU A ROSE GARDEN: What we have here is… failure to communicate. The problem you’re both running into is that while you’re both speaking, you’re not being UNDERSTOOD, and those crossed wires are leading to everyone getting annoyed or — in your case — disappointed on the regular.

The problem here is that the two of you have different communication styles, especially in how you communicate love and affection to one another. I’m sure you’ve heard of The Five Love Languages before; while people can (and frequently do) quibble about the accuracy or specificity of the “languages”, the concept is legit. Different people have different ways of showing their partners how they feel. One person may express love for people by giving gifts, because they like being able to provide little hits of joy for people they care about. Another person may express their feelings through words, or through making sure that the people they care for are provided for and want for nothing.

However, the problem that frequently arises is that sometimes our partners may not see that as expressing love and affection. Just as we have ways of showing that we care, we tend to have ways of wanting to RECIEVE love too… and sometimes the way one person demonstrates it and the other person receives it can clash. Somebody who is very concerned about paying their own way and supporting themselves, for example, may be uncomfortable with receiving gifts, no matter how well intentioned. Another person may have all of their needs provided for and live a secure lifestyle, but feel unloved because their partner doesn’t express love verbally or doesn’t spend a lot of time with them.

When these communication styles clash, conflicts arise. Both parties start feeling upset because here they are shouting “love” as loudly as they can, but getting nothing back and wondering why their partner is so cold or closed off.

And it only gets worse when the people involved don’t get that. While it’s very easy to say “I prove my love via X”, it doesn’t help as much if that’s not the love language your partner speaks or understands. It’s the “Ghost” conflict; Patrick Swayze may be saying “I love you” when he says “ditto”, but that doesn’t mean that it hits the same way.

And while yes, it’s important for people in a relationship to learn how their partners say “I love you” or express affection, it’s also important that they learn how to “hear” what their partner is saying too… and to make an effort to speak that language. Because even if someone “should know by now” how you feel… it’s still nice to be reminded every once in a while.

Case in point: you express your love by getting things for your husband, and you’d like the same in return — in this case, some flowers. The way your husband thinks about and shows love doesn’t follow the same lines; he’s not the “buy gifts to show love” type, and so it doesn’t occur to him to do so. And while that may well be true — it’s a foreign language that he’s not fluent in, so it takes conscious effort to “think” in it — that doesn’t change the fact that hey, it’d be very sweet of him to make the effort.

You may know he loves you by virtue of the fact that he married you, but that doesn’t mean that you only ever wanted to hear “I love you” once, and never again. After all, part of what helps keep a marriage alive and vital is to stay affectionate and flirty. Gomez and Morticia didn’t get to where they were by never reminding each other how much they loved and desired each other.

So no, you’re not being unreasonable by being upset over this. You’re definitely not asking too much. You’ve made an entirely reasonable request — you would like your husband to show love for you by surprising you with flowers — and he says “it’s not his thing”. While that may be true… that’s not really much of an excuse. It may not be how he shows love, but it’s also not something so outside of normal behavior that it would be an impossible challenge for him. You’ve asked for something so common that it’s practically a cliche, and he doesn’t seem to grok it.

Well… since we’re already talking about communication, it’s time to use your words. Just a little more bluntly and directly. While I know you would prefer to be surprised — that it be a spontaneous display of affection from him — sometimes you need to take the bull by the metaphorical horns and say “LISTEN UP, MOTHERF--KER.”

Tell him, straight up, that this is actually important to you. That while you know this isn’t how he shows love, but it has meaning for you and that this is something you want from him. He can set a calendar alert, set up a reminder on his smartphone or even get on his computer that night and schedule a delivery for a random day in the future… but you want this gesture from him.

It may not be quite the same as it being completely unprompted and spontaneous from him this time, but letting him know that no, this is has a LOT of significance to you might make him realize that this is a very simple thing he can do that would make you happy.

But none of that can happen until you stop hinting and start just straight up telling him that this is something you want from him. After that, you two can have a longer discussion about how you prefer to give and receive love… but first, tell him you want some flowers.

Good luck.

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

Marriage & Divorce

Next up: More trusted advice from...

  • Enjoy That Morning Cup of Joe -- and Its Health Benefits
  • Fall-proofing a Home Helps Keep Older Adults Independent
  • Monkeypox a Less Severe Cousin to Smallpox
  • Retiring? Your Tax Return Will Look Different
  • Dealing With a Bear Market
  • Over 60? Watch Out for Fraudsters
  • Grandparents' Executor Liquidates Everything
  • Son Isn't the Repairman He Thinks He Is
  • Invisible Roommate Proves a Mixed Blessing
UExpressLifeParentingHomePetsHealthAstrologyOdditiesA-Z
AboutContactSubmissionsTerms of ServicePrivacy Policy
©2022 Andrews McMeel Universal