Geek Advice – Dating Within A Circle of Friends

Dear Pink Hair Girl,

Among me and my friends, most of us in our mid 20s, I’m one of the only girls who hangs out in the regular group. So for the first time in a while I’ve been single for a few months, and to no one’s surprise, some of my guy friends are starting to show signs of liking me as more than just a friend.  Two in particular are laying it on pretty thick, I’ll call them Mario and Luigi.  Now this is already kind of a messy situation, but what makes this whole thing even more screwed up is that I’ve got feelings for Mario, and definitely not Luigi. I’m pretty sure the rest of the guys are just flirting with me while they’ve got the chance, since I’m single (at least I hope that’s all it is).  I’d really REALLY like to try dating Mario, but I’ve been friends with Luigi for years and don’t want to hurt his feelings. I’d be turning him down no matter what, but I know seeing me with Mario is going to hurt him a lot more than just a rejection. We all share the same friends, so it would be hard for him to avoid seeing us.  I’m considering dating Mario secretly, without telling the rest of the group for a while, but then that presents a whole other set of problems.  What’s the best way to do this to keep things with my friends going as smoothly as possible?

Peaches in Peril
Dear PiP,

Boys will be boys, and now that the girl who they already know is fun to hang out with is on the market, they’ve gotta test the water. That part is human nature. Some of it is probably harmless and just fun for them, but it is serious business for the ones who’ve started to develop actual romantic feelings towards you.  You hope it’s just Mario and Luigi that you’ve got to carefully consider feelings for, but it’s possible that Shyguy is in there, unable to step up and really contend with them because he’s the kind of geek who’s not good at flirting.

You also may want to be extra sure that Mario isn’t taking the flirting thing too far and that he’s genuinely interested in a serious relationship with you in before you set your sights on him. Making a wrong move in this emotional minefield might send the whole group exploding into Awkward Town. So honey, calling this a messy situation might be the understatement of the year.

Now, I don’t happen to personally know what your group dynamic is like. I’m hoping that you’re all mature adults who have learned how to deal with social unease or rejection with grace and underst–aw, who am I kidding? No one does that. Fuck it. I’m gonna assume they’re all flaming emo angerbabies, and I’ll prepare you for the worst case scenario. You’re going to have use your own knowledge of how your group handles social awkwardness to gauge how far to take my advice.

Talk about this with them. By this point, I bet everyone in the group knows the score anyway. Your friends probably know there’s some sort of battle for your affection happening beneath the surface of your group hangouts. At the very least, they can see what Mario and Luigi are doing. And they probably have not said a word about it to each other openly in any amount of seriousness. It’s possible that they’ve joked with each other about the fact that they flirt with you now, but as far as discussing the effects of this on everyone’s feelings? Nah. Probably not a word.  Do not count on them to smooth this over with one another. Be prepared to take the brunt of serious conversations about this onto your shoulders. This is important, because if feelings go unnoticed, this becomes a breeding ground for resentment later.

Imagine all you guy friends were raised by Homer. It might help.

To better your chances of things going smoothly, make sure you keep yourself open to discussion about all this. Don’t let it be the Chain Chomp in the room that you all pretend isn’t there. Start talking to them individually about the fact that you’re getting hit on a lot, and express your concern that it might make things awkward down the road. And if opening yourself up to discussion about this doesn’t get any possible Shyguys to come forward, then there’s nothing more you can do for them.  The bonus to talking about it with individuals is that you can gain some insight. Getting some bro-perspectives (brospectives) on the matter might reveal feelings among the group you didn’t know were there.

Figure out where Mario stands. And by figure out, I don’t mean go asking everyone what they think.  I mean go up to him and ask him if you guys are just flirting and having fun, or if he’s at all interested in dating you. You said he’s laying it on thick, but it’s quite possible that he’s the opposite of Shyguy, flirting way more than he means to because he knows you well and feels comfortable and gutsy around you. Finding out what his deal is will make it easier to take decisive action.
  • If he tells you that he’s just flirting, or might like to date you casually, then I highly suggest either letting it drop (because that shit gets complicated if you’re not already good at it), or hanging out with him away from the group to do your casual thing. If your relationship doesn’t make you exclusive to one another and doesn’t affect how you act around each other in a group setting, then it’s not important to announce it to everyone (unless it does eventually become steady dating). If anyone asks, be honest. Say that you guys are hanging out one-on-one, but that it’s not serious. The rest isn’t their business if you don’t feel like telling them.
  • If he tells you that he’s interested in something serious with you, and you feel the same way, then tell him you need to pace yourselves because a serious relationship means being a couple in public. If you plan to be serious about each other, DO NOT date secretly. This will mean you’re hiding things from your friends, which is hurtful to the group.  Explain to him that being a couple among the rest of the group might be awkward for everyone, and painful for Luigi. And yes, if Mario is serious about dating you, you need to tell him explicitly that you love Luigi as a friend and are worried about his feelings getting hurt as a result of not only rejecting him, but also forcing him to accept the two of you as a couple on top of it. A good boyfriend will understand that you have to treat the people you love with respect and patience, even if it means taking this slow with one another.  I’ll get into the whole ‘taking it slow’ thing right after the very next vital step.
Sad Luigi fanart. Unsurprisingly easy to find.
No matter what, confront Luigi. Whether or not things pan out with Mario, it’s important that Luigi knows as soon as possible where you stand with each other in terms of romantic feelings.  Find a time you can see him in private, face to face. Let him know that you’ve noticed the flirting, then tell him how you really feel about him. If he’s developed feelings for you, then shutting him down is gonna suck, for the both of you. But letting him hope that you two might be more and just letting him hang like that is even worse in the long run. Make sure he knows that you care about his feelings and don’t want to see him hurt, but that you also can’t force yourself to like him back–any more than he can snap his fingers and stop having feelings for you. In the case that you and Mario are starting to date seriously, you will also want to consider being the one to break this to Luigi.  I know, I know… it feels like throwing a red shell at him after he’s already spun out on a banana peel. But the alternative is that he’ll hear it through the grapevine, and then have to face those feelings alone. I guess it depends on how you think he’d prefer to find out–in either case, it won’t be kept a secret from him.  You can either be there to talk to him about the pain he feels, or let him handle it by himself.

Introduce new relationships within the group SLOWLY.  That is, feel free to let your relationship progress naturally when you’re hanging out with each other one on one. But if you get the feeling that you two being a couple around everyone else would make them feel weird, then take it easy. Be very deliberate about attendance. After you’ve made it public knowledge to people in the group that you guys are dating, stagger your appearance at hangouts. Organize ahead of time so you can go to a couple group hangouts without him being there, and he can be there without you around. Yes, it means spending a couple nights on your own or with some other friends, apart from each other (I know it’s tempting to be together 24/7 at the beginning of a new relationship), but it can really help ease things with the rest of your mutual friends.  It lets them see each of you as the same individuals as you were before, but with the knowledge that you’re a couple.

I'm so glad someone drew what I was thinking for this.

They don’t have to see hand holding or longing glances or hear your inside jokes fly back and forth in mixed company just yet, so this approach gives them time to let the idea sink in without actually seeing it. This will make them all more prepared for when you do finally show up to the group together. And when you do, be yourselves–but go easy on overt displays of affection. PRO TIP: Discuss the fact that you two will not display affection openly around friends for a while. Make sure you both know what’s ok and what’s not, to avoid one of you feeling rejected when the other brushes off affection in front of the gang. It’s hard for new couples to hold back sometimes, but do everything in your power to lay off around your friends–especially if Luigi is there.

Sisters before Misters.

And speaking of Luigi, he’s going to need some space. Rejection is embarrassing enough, so he will likely distance himself as your friend in any case. Try not to take this personally–it’s usually not meant as a punishment.  Ultimately, it will be up to him to determine how he handles seeing you as part of a couple. Always offer to be there and hear him out, because chances are it will be painful for him for a while. Or, if you two aren’t comfortable talking, tell a mutual friend that you’re worried about him and make sure that someone makes themselves available to talk to him about it in your stead.  As long as you’ve been honest with him, he has to learn to accept rejection and respect you as a friend.  If that means not being around your friends when you and your new boyfriend are there, then its up to him to make himself scarce.

By now, I hope that everyone reading this has painted a beautiful Super Mario Brothers soap opera-esque video game scene full of Princes Peach dodging Bullet Bills, Shyguys secretly picking flowers only to get jumped on, and plumbers with giant mustaches either flirting or staring teary eyed into the distance. Yoshi’s in there somewhere, just licking things for fun. That’s honestly how I’ve imagined you and all of your friends now. But for you, PiP, I wish the best of luck. These might be murkier waters than that of a sunken ghost ship full of Boo Buddies. Navigating them will take a lot of patience, courage, and some extra mushrooms- err skill.  My one final bit of advice is that if all this boy drama has got you feeling exhausted… consider spending more time with Daisy.

Pink Hair Girl
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Pink Hair Girl

After her DNA was spliced with that of a jelly fish, Olivia became known to all as Pink Hair Girl. She also gives advice to geeks all around the world.


  1. *stares teary eyed into the distance*

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