Sooo Orlando,
Me an my ex broke up like SEVEN months ago and I still see him around. The problem is, his friends are my friends and my friends are his friends, so it’s inevitable, ya know?? Now, every time I see him its totally weird and awkward between us because obviously, neither one of us want to be there. I have no idea what to do cuz I’ve tried not to be around as often but it’s been seven months and things are still strange. What should I do?
Thanks,
The 3rd, 4th & 5th Wheel

Dear 3rd, 4th & 5th Wheel,
Seems like you’ve got yourself in a bit of a community conundrum. I suppose the right sort of advice to start with would be the old, do not crap where you eat. This is why you do not date people in your group of friends. It eventually makes things so awkward that someone gets dropped from the inner circle, either by their own volition or the group’s. Now you’re faced with that crossroads. You can’t stop things from being weird between the two of you, that’s a major part about the end of a relationship. So the way I see it, you have two options:
- Option 1: You get over it and grow up. It’s over. Part of the reason it’s really uncomfortable is because you’re making it that way. Obviously, you can never have things go back to the way they used to be, so you’re going to have to man up and act like an adult. This means realizing that you’ve got to move on. Just do it.
- Option 2: Reorganize your group of friends. There, I said it. Sometimes, that sort of weirdness is just not worth the trouble of the friend group. I suppose this is the last thing you want to hear, but honestly, if you cannot deal with seeing him without making things horrific then you need to remove yourself from the equation entirely.
Hopefully you’ll take this advice in stride, as well as realizing that you’re obviously apart of the problem, so if you want it to end it’s up to how you behave in the future. Either that, or you can keep on doing what you’ve been doing until your group of friends intervenes and let me tell you, that won’t be pretty.
Forever,
Orlando
Dear Orlando,
Recently I found myself in a battle with my Ex over various social websites like Facebook and Twitter. After we broke up we decided to still be friends and keep in contact, but things went terribly wrong. I was out with friends when I ran into him drunk and he was all over some girl that we both know. I was disgusted and pissed that he was doing that right in front of me! When I got home I went on Facebook and changed my status to: OF ALL THE THINGS I HAVE EVER BEEN A DRUNK RAPEY A$$HOLE IS NOT ONE OF THEM. This begin a week long war between us on Facebook and Twitter, ending with me deleting him as a friend. Should I never bring him up on there anymore? I am just so mad that I want to continue to comment about what an idiot he is. It is my right to use social networks as I please, right?
Sincerely,
Tweeting with fury

Oh Tweeting,
You made one of the cardinal mistakes of social networking: b*tchin’ about an ex out of frustration to get attention from them. Let’s face it, you went out of your way to go home and let him know online what a piece of crap you thought he was. If homeboy had the tiniest bit of intelligence he’d have deleted you the second he saw your status update and ignored you FOREVER. Obviously, the two of you have unfinished business, but get a grip and some self worth. Bickering over Facebook or Twitter does not make you a lady, it makes you a child, like Miley Cyrus, who’s been in some heated exchanges with her own ex Justin via Twitter. Take it from me, if you really want to hurt a man ignore him forever and move on with your life. Nothing burns like knowing you cannot phase someone anymore.
Love,
Orlando
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Dear Orlando,
My job is stressful, I live in a cluttered studio apartment, I’m always having drama with my boyfriend, and I feel socially obligated to hang out with my friends all the time, going out to drinks and movies and spending money I don’t have. How can I simplify things so my life is less chaotic?
Yours,
Stressed

Dear Stressed,
I find that when I’m freaking out about my life the best thing to do is to clean. If your personal space is clean, then you will be able to relax in it. Since the weather is warming up outside (finally…GO AWAY JUNE GLOOM!), now would be a good time to go through your wardrobe and your apartment and get rid of anything you don’t need or wear anymore. You can make a little cash for many of these items by taking them to Crossroads Trading Company or Out of the Closet. Personally, I like Out of the Closet because they donate their proceeds to AIDS research and health care. You’ll be surprised at how relaxed you’ll feel after you know that you’ve helped the world by donating your old clothes and housewares to a good cause (or gotten cash for them). Once you have gotten rid of EVERYTHING you possibly can get rid of, go to The Container Store to find ways to organize the items you have left so your apartment will look neat and tidy (also check out Ikea, they have tons of organizational ideas). I know this is starting to sound like a commercial, but I actually do love all these stores and think they can help you. In terms of friends and feeling like you have to hang out with them, you need to learn the power of pretending. Tell them your mom’s in town and you are going to dinner. And then stay in and watch a movie. Tell them you’re going out of town on business. And then stay inside and read a book. It sounds like you need a vacation from your friends, so take one! And as for the boyfriend with the drama, you need to ask yourself if you’re interested in the drama or him. But mostly, clean up your space and get organized. It will make your life feel WAY less chaotic. I promise. YAY!
Love,
Orlando
Dear Orlando,
I hooked up with a friend-of-a-friend a few weeks ago and now it’s awkward. We see each other all the time because we are both close with our mutual friend. He’s totally cute and I’m into him, but I’m not sure if I want to pursue anything more yet. Every time we hang out with our group of friends it’s kinda weird. How can I make this situation less awkward?
Yours,
Some Rando Chick

Dear Rando,
I’m sure your hookup is feeling just as awkward as you are. In this situation, humor can be really helpful. Next time you see him, say something like “hey remember that one time we hooked up and then pretended it never happened?” This will get the ball rolling on acknowledging that you’ve hooked up and bring it into the open. There’s no sense in feeling embarrassed about hooking up (Not that I’m condoning random hookups…be careful out there and always be SAFE!). In other news, you’re obviously compatible in some way if you share close friends, so keep your mind open to a more substantial relationship. You never know where things will lead but the best way to make sure things progress is to keep an open dialogue. Bottom line, say no to awkward by taking the lead in bringing things out into the open.
Lovebubbles,
Orlando
Dear Orlando,
Last fall, I was laid off from my job as a paralegal at a law firm (the firm subsequently went under and no longer exists). Additionally, I broke up with my boyfriend of five years and haven’t been on a date since 2003. I find it difficult to hang out with my friends because they are all really happy all the time. I find the more things go wrong in my life, the more it seems like everyone else’s life is perfect. How can I have a happy life when I spend all day submitting job applications that get no response and stare at all the piles of bills that I can’t pay? Life sucks right now, how do I make it better?
Yours,
Over It
Dear Over It,
After being busy and used to having your schedule monopolized by a time consuming job, you’re probably not used to having this much time to think about everything that’s going on in your life. First of all, I’d suggest you do something nice for yourself every day. Go to a magazine stand and look at all the tabloids or check out something in LA you’ve never done before (try taking the subway from Hollywood to Downtown, it’s surprisingly fun and exciting). Also, you have to stop feeling bad about being unemployed. There are tons of unemployed people right now in your exact same situation. You are doing all you can to get back on your feet and that’s the best you can do.
Secondly, you need to disconnect your emotions from your monetary situation. Surely, money is important and you need to deal with all of the financial difficulties that come with losing a job, but there are far more important things in life than money: your health, your family, your happiness, etc. Make a commitment to yourself that you will tackle your financial woes and then put it out of your mind for the rest of the day.
Finally, if you are unhappy, you can feel free to tell your friends. You don’t have to fake happiness for their sake. I’m not saying you should turn into a total Debbie Downer, but it’s okay to acknowledge feeling a little down about all the things going on in your life. Your main goal should be to have a positive attitude, but don’t feel guilty if you can’t be Happy Harriet all the time. Everything is going to get better, especially if you keep focusing on the fact that everything is going to get better. Use your time off to do stuff you know you wont have time for when you get a new job because when you’re working again, you might miss these decadent days of free time.
Love,
Orlando
Dear Orlando,
Two of my best friends are a couple. For the purpose of this letter I’ll call them ‘John’ and ‘Jane.’ We’ve known each other since college and I love them both dearly but they drive me crazy by always canoodling everywhere we go. For example, they’ll be like “Come over for a movie!” and then I’ll go over and we’ll watch a movie only to have them snuggling and making out the whole time. They also like to make out at the bar which is really annoying, especially if it’s just me and them. They like hanging out with me, but always manage to make me feel like a third wheel. Their constant making out grosses me out, what should I do?
Yours,
I Hate My Friends

Dear Hater,
You need to limit the alone time you spend with these people. Obviously, they are good friends so you don’t want to cut them out of your life. But you shouldn’t put yourself in a position where you feel like an unnecessary member of the group. If they invite you over to watch a movie, bring a friend. That way, you and the friend can make fun of them later without them ever knowing you find their makeout sessions disgusting. If they start making out in a bar, walk away and pretend like you’re going to use the restroom to throw up. Repeat this every time they start making out. This might help them get the hint that their constant canoodling makes you wanna barf. You could also try being direct with them and telling them it makes you uncomfortable when they are overtly intimate in front of you, but that would be way less fun than your other more creative options.
Love,
Orlando
Dear Orlando,
I am a 23 year old woman and I work as an assistant at an ad agency. I met an older guy at a networking event last fall and we’ve been hanging out ever since. At first, I was totally into him but after thinking about it and hooking up with him a few times, I decided that I should stop dating him. He’s great and I’m attracted to him, but he’s 45 and in a totally different time in his life. While I toil away as an entry level peon, he works in an executive role, makes a ton of money, and has a house in Brentwood. While I’ve made it clear that I don’t want to date anymore, he still likes to go out and enjoys my company so we go out to dinner a lot and he always pays. I know it’s kind of weird, but I feel like if he’s enjoying himself it doesn’t matter that he’s sort of buying my attention with fancy dinners. He recently invited me to accompany him to the South of France and I’ve never been abroad before so I’m tempted to go. I’m conflicted because I don’t want him to get the wrong idea. I mean, a trip to France seems like something for honeymooners. But I want to go to France. What should I do?
Yours,
Wannabe World Traveler
Dear Wannabe,
While I’ve always dreamed of having a sugar daddy to take me to France, I’ve watched a few friends go on ’round the world trips with Older Dudes and it always resulted in total awkwardness and semi-co-dependency. I would say going is probably a bad idea. It sounds like this guy still has a thing for you, and you’re just making it worse by continuing to hang out with him. You sound like a smart girl to me, so I’m sure you’ll eventually figure out how to travel the world on your own terms. That saying “there’s no such thing as a free lunch” applies here. While it seems like the trip is free, you don’t know what kind of reciprocation your older gentlemen friend expects. And I’m not just talking about sex here. Unless you want to feel emotionally and socially indebted to this guy, I would tell him “no, thank you.” You have your whole life to travel, so don’t feel like you have to do it all right now. This week’s mantra: free is not always free. Sorry babe.
Lovebubbles,
Orlando
Dear Orlando,
My friend Jazmine never calls me or wants to hang out but whenever I run into her at a bar she acts like we’re best friends and says things like “I miss you! How come you never call me?!” and then tells everyone we’re best friends. She drinks a lot and gets totally crazy and says things like “The phone works both ways, honey!” It’s weird, because we rarely see each other but when we do it’s too intense for me because she’s always wasted and way too needy. How should I deal with this situation so I’m not constantly being accosted by her when she’s drunk?
Yours,
She’s Not My Friend
Dear She’s Not,
It sounds like your friend may have a drinking problem which is adding to you difficulty relating to her. I would talk to some of Jazmine’s closer friends and ask them what they think about her and her drinking habits. You’re not a doctor but you should express your concern if you think she’s always blitzed and acting crazy all the time. As far as dealing with her neediness, I’d let her know (when she’s sober) that her actions seem a little extreme to you. You can put it nicely, just tell her you’re concerned. It’s hard to work through friendship issues with someone who is drunk so I’d recommend making a commitment to meet up for lunch or shopping or something. If you still feel uncomfortable with her neediness after spending quality time together, let her know you need to cool it off a little bit. If this doesn’t get her off your back when you run into her at the bar, I’d start wearing costumes when you go out. Maybe dye you hair and wear sunglasses or something. Then maybe people will think you are famous and buy you drinks. Just a thought.
Love,
Orlando
Dear Orlando,
My friend ‘Amber’ is always talking about how much guys like her and how it’s so difficult not being able to get people to take her seriously because of her looks. We’re sort of opposites. I’m more the introverted type and she’s totally extroverted and willing to talk to anyone. I love spending time with her because she totally inspires me to be more forward, but sometimes her over-confidence gets on my nerves. How can I tell her to cool down all her self-promotional speech without damaging her self-esteem or making her feel like I’m judging her?
Thanks,
Friend of Popular
Dear Friend,
Amber sounds totally annoying. I can see why you are friends with her, though, and think she has a lot to teach you. Most of us could use a little inspiration to be outgoing so I think you should keep her around. Most girls who spend a lot of time telling you how cool they are actually don’t feel all that cool on the inside. If she actually believed she was cool, desirable, and fun she wouldn’t need to run around telling everyone so all the time. So, in order to make sure that she doesn’t keep blabbering to you about how rad she is all the time, I’d stop responding to her when she does so. For example, when she says stuff like “I went on a date with this guy but I can’t tell if I like him because all these OTHER guys like me too!” pretend like she’s speaking French or some language that you don’t speak. After a while, she’ll start to get it and start understanding that what she’s saying is totally not interesting to you. If that doesn’t work, dump her. There are plenty of outgoing friends to meet in this gorgeous city, and finding ones that aren’t completely conceited could be just the social exercise that you need. YAY!
Kiss,
Orlando
Dear Orlando,
I am from Texas and a girl I grew up with recently moved out here from our hometown. I’ve been out here a few years so I’ve developed my own social network. She contacted me on Facebook and asked if we could meet up and I offered to take her with me whenever I go out. That was three months ago and I’ve been dragging her around the whole time. She doesn’t express that much interest in me, and seems mostly interested in meeting and befriending everyone I know so she can grow her social circle. I know this is a natural part of settling in to a new city, but am I morally obligated to continue playing babysitter? She’s kind of annoying and arrogant and my friends are not that into her. Can I dump her?
Yours,
Go Away Girl
Dear Go Away Girl,
If you don’t like this girl and your friends are not taking a liking to her, you’re not doing her any favors by hanging out with her. She deserves to spend time with people who share her interests and actually like her personality. You deserve to hang out with someone who isn’t totally annoying and full of herself. So you should probably break it off. But don’t do it in a mean way. Someday you could move to a new city and might need the help of an old acquaintance to get you on your feet. I would tell her that you want to spend time alone with a few of you old girlfriends and have a night out without her. You should still invite her to large parties where you can let her roam free out of your presence (hey, maybe someone at the party will be into annoying people!) It’s good karma to help her succeed socially, even if she seems like sort of a reject to you.
Love,
Orlando
Today’s mantra: Treat her like you’d like to be treated. You could be in her shoes someday.






