Ask Alyssa: “Should I ask my boss on a date?”


Well hello-o-oooo! I hope that 2013 is treating you all well so far. I’ve been MIA for a minute, but now I’m back and ready to dive right back into all of your questions! This week I answered some interesting questions, some, lets just say “deeper” than others but all good none the less. So without further ado, here are this weeks Q and A’s by yours truly!

Childish Games

Hey Alyssa, I had this friend who during summer told me she liked me. I am really not a relationship type person and never even thought about her that way, so I turned her down. She was kinda OK with that, but informed me that I should never talk to her again, cannot tell anyone why we are no longer friends and that she would delete my phone number and e-mail, etc. So, OK, I can understand that, somewhat — but, since we both study the same thing and are in the same class, things have gotten a bit complicated. She has told me that I cannot talk to people she’s talking to, and can’t even comment on anything school-related she does, even when it’s something that other students are expected to contribute to.

I have tried to adhere to her rules. I recently decided I should try and talk to her about this because it’s been kinda straining on our mutual friends, whom she uses as messengers when she wants to complain to me about something. Well, the talk didn’t go well and now she apparently blames me for everything, and is retroactively angry at me for everything I’ve said and done ”wrong” during the time I’ve known her. So, my question is, how should I deal with this thing? I fear it’s starting to be a bother to our other classmates as well. — Troubled24

Dear Troubled, This person sounds like a giant irritating baby. I’m sorry, but for god’s sake tell her to grow the hell up. You need to get one thing straight; YOU, did absolutely NOTHING wrong. If this girl liked you and you didn’t have the same feelings for you, I applaud you for not leading her on. You were straight up honest and said you were not interested. BAM! Over and done with.

I can understand her maybe not wanting you to tell people that you shot her down, I get that — but she has no other hold on you and should have zero expectations for how you move through the world after that. If you not being intimately interested in her caused her to decide that she didn’t want to be friends any more, she wasn’t your real friend to begin with, as for school, she needs to deal with it. You can talk to who ever you want, you can comment on anything you please and when it comes to school NEVER let anyone get in the way of your education. NEXT! Best of luck, Alyssa

Daddy Warbucks

Hi Alyssa. So, this might be weird, because I know mostly girls write in, but I like reading your column and I liked watching you on the show. You were the only one who wasn’t completely insane or overly dramatic and most of all you seemed the most relatable.

Anyway, I have been with my girlfriend for a little over four years and I think she is the one. I plan to ask her to marry me in the fall since its her favorite time of the year. The thing is, she is from a kind of poor family, and I was fortunate enough to be born into a family with money. I took over my father’s business and have had to do very little to get all the wonderful things I have in my life. My girlfriend always talks about how she doesn’t need much, and that she feels uncomfortable around people with lots of money. She is a wonderful, bright woman, she put herself through school and worked three jobs when we met. I had to force her to quit one and lied to her about how much her half of the rent was when we decided to move in together so that she wouldn’t have to work so hard. I wanted to pay for everything when she moved in but she would not have it. I respect that, but want to treat her the way I think she deserves to be treated. I want to give her a beautiful ring and an amazing wedding and tell her that she only needs to work if she wants to. I’m just worried that she will feel uncomfortable about everything and/or take it all the wrong way. How do I make her understand where I am coming from without making her feel uncomfortable? -Brian

Dear Brian, are you for realsies? First world problems! Kidding. Well, here’s the thing: You guys have been together now for four years AND she moved in with you, so she obviously gets that you’re not trying to force your silver spoon down her throat.

That being said, I think that you should be attentive to what her likes and dislikes are. I think you’re already listening to your heart and that its telling you what to do. You paid attention to the fact that her favorite time of the year is fall and you know how she feels about super extravagant things. I would start there. Don’t be over the top, don’t run out and get a huge ring, because that’s not what defines your love for each other. Get her something just a little nicer than practical.

As for the wedding, if she says yes, plan it together, the rest should fall into place. She may never become totally comfortable being lavished with gifts, or impressed by a bank account but that’s probably why you click. If you want to spoil her do it in ways that she would like and continue to be attentive. I hope that helps! If it doesn’t, I’ll put you in touch with my mom. You sound like her kind of dream boat. XO — Alyssa

Sexy Boss

Dear Alyssa, I work in a boring office building in downtown Boise, I am not completely out and I am 26 years old. Recently our office went through some changes and we got a bunch of new managers and bosses. I am essentially a glorified secretary. I am 99% sure that my new boss is gay. She is super hot in that kind of andro way and I’m pretty sure I heard her on a call with a friend in her office talking about a lesbian movie.

Anyhow, I am super into her. I find every excuse to go into her office to talk, but she doesn’t seem interested at all. She is very nice to me, but barely looks up. What do you think I should do? I mean, I’m not even sure she likes girls — maybe I’m just assuming because I want it to be true. Help! Sincerely, Amanda

Dear Amanda, Here is the thing about office crushes, sometimes you never know who is interested or not because you are at work, you know — working. You have the double whammy of it being your boss and not just a regular co-worker.

I’d say, ask her out for friendly drinks after work or something like that. Get her out of the office and talk, get to know each other. You don’t really know much about her at all, maybe she’s already in a relationship and that’s why she seems disinterested — who knows? It’s too soon to tell. For now, lay the ground work, get to know her and try to make a good impression. Baby steps young Skywalker, baby steps. XO — Alyssa

Tough Love

Alyssa, hi. I am 30 and have been with my partner for 10 years. She is an alcoholic. I love her but just can’t do it anymore. We have been on a roller coaster of a ride for the last six months. She crashed our car, she almost died and that still isn’t enough of a wake up call for her to get help.

Everything else in our relationship is great, when she is sober, but when she isn’t its like living in hell. We barely ever go out anymore because if we do she drinks to the point of blackout. All of our friends have basically shunned her. Its really sad, most of them only call me in secret if they even call at all and only want to see me because they don’t want to have to babysit her if she comes out. It’s awful. She is constantly falling down, she has a new cut, gash or bruise every other week and it’s embarrassing. I’m afraid if I leave her that it will be the straw that breaks the camel’s back. I barely sleep anymore and if I do its because I am crying so much that it knocks me out.

She is so talented, bright and beautiful. When she is sober she has the world eating out of her hands but she has gotten so bad with drinking over the last three years that no one will give her the time of day. I don’t even really know what I’m asking. What do I do? – Emily

Dear Emily, This is a really tough place to be in. I have known people with alcohol addictions and it’s not an easy hand. Its tough to turn your back and yet its nearly impossible to work through. The truth of it is, with addiction, you can’t heal or help someone unless they want it for themselves. At this point it sounds to me like she needs professional help. Addiction is super sad because the addict often is a shell of their former self and everyone can see it but them. Most of the time, sticking around only enables the addict to keep doing what they are doing. I am a firm believer in tough love; I give it to all of my friends. I would try to set up some type of intervention.

I know it sounds cliché, but this method really does work. Surround this person with people who love her and let them tell her why they have disappeared out of her life. She may not want to hear any of it, but it will be your chance to tell her that if she doesn’t get help and make a change that you can no longer be with her anymore. Some people have to hit rock bottom, and rock bottom doesn’t involve you continuing to take care of her and clean up her messes. I know it may be hard, but you said it yourself, you just can’t do it anymore. If there is any chance for the two of you, it will only be once she has gotten herself clean and gotten her shit together. I’m not sure where you live, but you can message me privately to tell me what area you are from and I’ll try to help you find a facility or psychologist who deals with drug and alcohol addiction to walk you through this tough but necessary task. With love and concern, Alyssa

If you have a question you would like me to answer, email me at! Don’t forget to follow me on twitter at @AlyssaMorganLA. xoxo!

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