Ask Jack

“Since the last ‘Jack and Jill’ segment had a guy wondering about penis size, I thought I’d turn the tables. As an itty bitty A-cup gal, I’m not overly conscious of it, but I do wonder how much it truly matters to a man. If a man met a two equally interesting women at a function, would he be more drawn to the woman with the normal sized (i.e bigger) breasts? Is that just, human nature?” – Jillian

Hey Jillian,

I know my answer will sound like a feel-good cop-out, but it’s the dead truth: breast size is only something advertising, pornography, and commercial establishments like Hooters concern themselves with. If a man is attracted to you, he is attracted to your breasts because they belong to you. Breast size is never a dealbreaker unless the guy has a crazy obsession with breast size.

There are several female physiques, and what they all share, as a rule, is everything being in proportion. Picture a bigger boned lady with little breasts, or a 100-pound woman with double Ds, it doesn’t equate to the natural beauty of a proportionate body type. Unlike penis size, which seems unfairly random, breast size matches physique (99 times out 100), and what you have looks right on you.  What you have suits you, and a man sees that. Yes, many “boob guys” love large breasts, but just as many men have breast preferences that focus on aspects other than size. Some like small nipples, others big nipples, some like closely spaced breasts versus the opposite. Some get more hung up on ‘hand feel’ than size. I wouldn’t get too hung up in the physical attributes of your breasts, and certainly not their size. I swear: if he loves you, if he’s attracted to you, your breasts are beautiful because they’re yours. P.S – just as many men have a small breast fetish. It’s a thing, an aesthetic thing maybe, so much so that every internet pornography website has a category devoted to Small Breasted Women.


“Hey, man. One dude to another. Is there a classy, effective way to encourage your woman to lose some weight? She’s at an all-time high here, lol.” – ANON GUY


No, asshole, there isn’t. My best advice is you leave ‘your woman’ so she can be with someone better than you (which won’t take her long). She deserves someone who adores her for something far more important than this month’s scale reading. Please slap yourself for asking that. I’m only answering it because there were only two questions for “Jack” this week, and this was one of them.

Ask Jill

“I feel ugly all of the time. I don’t know how to stop feeling that way. It makes me sad. I feel like I poison everyone around me with all my self-hate. How do I stop hating myself and feeling ugly? What do I do? – Ugly

Oh! It is so tough to feel amazing sometimes. I completely get it.

A few years ago, I got really tired of hating myself and I tried every single day to focus on the good things about me. I made a list of compliments people have given me to look at when I felt low … compliments on beautiful things about me that I never really saw. As cheesy as it may sound, I started to make a point of finding one lovely thing about myself every day. It could be the tiniest of things like how adorable your earlobes are or how amazing it is that you’ve inherited your grandma’s strong jawline. I poured through body positive blogs on Tumblr. I tried to stop talking shit about myself to my friends. (Sorry Megs, I know I still do this sometimes. Forgive me?) I made a promise to never talk shit about myself to my partners/lovers.  When I would find myself thinking horrible thoughts when I looked in the mirror, I actually would stick my tongue out at my reflection as if I was a bratty seven year old girl and not a thirty something year old woman. Funny enough, it eventually started to work. I don’t feel ugly all of the time, just some of the time and I think that’s pretty natural. It’s ok to have bad days sometimes, just not all of the time. But you better believe that even on my bad days, I make a point to see something good. I am by no means, the most beautiful girl in the world, but a lot of the time I let myself feel like I am.  Perhaps it seems silly, but it really did work. I thought positive thoughts and over time, it really paid off.  There’s a quote from a Roald Dahl book that I’ve always absolutely loved, even when I was younger.

“A person who has good thoughts cannot ever be ugly. You can have a wonky nose and a crooked mouth and a double chin and stick-out teeth, but if you have good thoughts it will shine out of your face like sunbeams and you will always look lovely.”

I honestly believe that. Even with my funny freckles and my chubby cheeks and my small mouth that I always wished were bigger and brighter, I am lovely and I bet if you stop and focus on the great things about yourself, you will see that you are lovely too. If crawling out of a fog of self-hate is too tough to do on your own, there is no shame in getting counselling. I believe Lemarchant House helps those struggling with decreased self-esteem, so try contacting them for more information. I hope that you feel better and lovelier and absolutely awesome really soon. xo.

“My wife and I have been married since 2008: I found out that she cheated on me about five years ago and have had a hard time dealing with it. Over time things got better and I let it go. Every now and then she starts acting out like she did when I found out she cheated the first time. So I started to look around and found things that worried me, like pictures on her phone and receipts for things she never told me about. I let it go because she had explanations for it all that sounded fine. But recently she started to act out again and I looked around and found notes about her going on dates and having sex with men while I was on deployment. She had sex with a guy in my house on my bed five days before my fifth anniversary. She says she can’t trust me because I snoop, but I can’t trust her because she cheats. What do I do? I want it to work but don’t know if I can deal with the emotional distress of her banging random guys.” – Caleb

Hi there,

I think that there comes a time when you have to just give up on someone. Unless you and your wife agreed to have an open relationship, her sleeping with other men is completely disrespectful to you and to your marriage.  I am completely confused as to why you would want this to work at all, after everything that has happened between the both of you. I can see forgiving her once, but nope, she shouldn’t get to cheat on you again and again and again. When you stay with her, you are giving her permission to walk all over you and to treat you unkindly.

And, of course you have had a hard time dealing with it! When trust is destroyed, it can be the hardest thing to rebuild. It’s not done in a day or two, not in a week, not in a month. Sometimes coming to terms with being betrayed can take years to get over. Sometimes, you never really recover from it.  I want to apologize in advance if I come off a little harsh in my reply to you. It’s only because I’ve been cheated on and lied to before and I have absolutely no tolerance for it.

As for your snooping? Don’t do it. If you feel you have to, you need to talk to her or you need to divorce her. I know it might seem better to be aware than to be completely oblivious, but snooping is not the answer. The answer, really, is to be in a relationship with someone who you trust and that you don’t feel the need to spy on. Snooping is just going to make you feel absolutely wretched and sneaky if you don’t find anything and if you do find something? You’ll still feel horrible. Sure, if you do find evidence, you can confront her but then what? It sounds as if you’ve already found a whole pile of shit and you still want to be with her. When you’ve been cheated on, betrayed in some way or lied to by someone who you love, you will start to suspect EVERYTHING. You over analyze and you play detective and you exhaust yourself looking for signs that someone is being sketchy again. It’s unhealthy and it’s exhausting. You either forgive someone and the both of you put in some real work to get past it and repair the relationship or you leave them. Those are the only two options.

I think you need to step back and re-think why you are still with this person. Getting out of a marriage can be so hard, but it will be worth it. You don’t have to live with a knot in your stomach. You don’t have to be overcome with jealously and suspicion constantly. You won’t be nervous every time that you’re away from her, wondering who she’s sleeping with. You can actually be happy alone or you can find another person that you can be vulnerable with and who will treat you like you are something to cherish, not like garbage.

Jack & Jill will each answer two of your questions, every second Tuesday (thereabouts). Submit, anonymously, with the form below

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