J.Z. Sherrington

Images of man in question below.

Let's say this hypothetical guy, at 24, is fairly fit and attractive and tall, tattooed and a musician and can speak a few languages. But he's terrified about his one insecurity which is that the thing he loves most about himself, that he waited for someone he loves, hinders him because women want a dude who knows what he's doing and don't want to have to teach a clueless guy whose last (and first) kiss was almost a decade ago. Plus at his age, odds are she's probably ****** a bunch of guys whereas he was busy with instruments, being socially inept and D&D.

What if he's never done anything at the age where you've probably been with a few guys and feels somewhat inadequate for it? Even if it's oddly a trait that he likes because he wanted to wait for someone he loves?

Would you value it as much as he does?

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Like if I put up $9k on a $45k loan? Is that possible? I don't have the best credit but I know lenders are sometimes more willing to lend if they receive some money down. I'm looking to use it for startup expenses for business.

There are so many things I'd love to say about her. It stings a bit right now because we've talked for a year and a half and I've harassed her for a drink and a dance for that duration. There was a period from September to March when we didn't talk because I crossed a bit over the line. But she messaged me back and we started talking again. And, inevitably, I started flirting again, I made it clear when we had stopped talking that I just can't stop so she messaged me back in understanding.

I kinda miss pre-pause though when she would actually flirt back and we'd have a little banter going. She told me a lot of stuff too, like how her husband is gay and she didn't really marry for love and they don't even sleep in the same room and haven't had sex in like five years. But she's also not really interested in anything and just wants to try and get her career started and also is married. I don't really follow that when you put in with the other stuff but I guess some people choose to be in loveless marriages?

She also has extremely low self-esteem and takes almost none of my compliments, consistently saying she looks like a monkey.

She's really smart and funny, quite a bit older than me, but that really doesn't matter. I like to think we have a good thing back and forth, chemistry. But, I guess I'm the only one who sees it.

I fell in love with a woman in her 40s. Problematic. Not only because I'm 22 and she my landlady but also because I'm a sentimental romantic and virgin and she enjoys ******* guys my age regularly.

Thing is, I have part of me that knows that shes just lonely and damaged as I am and is just doing it to fill a void. And the other part of me keeps reminding that I dont live in a ******* rom com. She flat out told me one day that she feels lost and is in a weird place in her life and doesn't know what she wants. She told me about two of the breakups she went through too and they sounded rough. I think shes hurt and just doesnt want to admit it to anyone. She spent a lot of money on her body, who does that unless they're lonely, right? and she has a ton of degrees, these guys dont realize how smart she really is.

She used to tell me how she trusts me and talk about herself but she barely talks to me now. I think I may have made her uncomfortable, I sort of poured my heart out to her and told her she was beautiful. Now I just want to go back to the beginning when it was fun and we could do things together and joke together and people thought we were dating. Lol.

I'm hopeless aren't I?

I'm 21, never dated before but I've been trying the last few months to little success which I dont get since I have a great career and think I'm decent enough. I used to work at a restaurant a couple years back and there was this waitress that I worked with who really annoyed the **** out of me but was super cute and I liked her and tried to get her to go out with me. I was (still am) also a virgin waiting for the right girl and shed jab at me about it all the time since she had sex by that point. Anyway, her boyfriend cheated on her and they broke up and I tried to cheer her up before I left the restaurant for school and she did too not long after. We started talking over Facebook recently about her **** (she once shoved one of my action figures down her bra to get me to Grab them, made me uncomfortable). I ended up just coming out with it about how I liked her and asked her to coffee which she agreed to but only as friends since she has a boyfriend. Made me really depressed. I said I'd still go but I mean I'm romantically interested in her and its gonna ******* hurt to see her again. I dont understand why we went through that whole convo only for her to mention her boyfriend. At this rate it feels like I'm being ******* punished for something. My best friend, who knew her longer, thinks I still have a shot but now I'm just depressed. If she's dating I dont have a shot and with my ******* luck that's how it is. I'm a good Protestant, I dont understand why I'm being punished?

So I'm a 21 year old man. Interested in my former high school teacher. She's a really beautiful and intelligent woman in her early forties. I know I pick the easy ones. I saw her recently when I went to my former school and she seemed rather happy to see me. We had a nice chat catching up but when I went to ask her for a coffee at the end I'm embarrassed to admit that I choked. Now I ****** up I know but here's my question...is there a way to unfuck it? I mean there has to be a second chance somewhere right. I've been running my head thinking "if I went back it might be creepy". I still have her email from way back when I was in her class I never weeded my contacts and thought about shooting her an email but that might be creepy too. Especially since, A: Those emails might be monitored and B: I'm really not sure what I would say at all if I even did.

So did I really just permanently **** this or is there a way to unfuck it? I mean we had a nice time talking and I was too ******* bitchy to actually ask. How do I get a second chance, is there one?

tl;dr: Went to ask former teacher to coffee, choked, is it over or is there a second chance somehow?

Alright, gear up, this is gonna be a bit...

So I met my gf about eight months ago after moving to Toronto for a music career and fell instantly in love. Kinda helped that she likes the German accent, guess it makes me sound gentlemanly (which, modestly, I am) but I was nervous because she was a bit older than me, had been out of University for a while and was a couple years older than me whereas I was 20 and fresh out of University. Then I learned, like me, she's a virgin and shy and the Lord answered my prayers. When we finally got to the deed, I realized she may be pure but she's far from as innocent as she let on. But my confidence got built to where I'm getting comfortable even taking the lead in everyday things, which I can tell she likes. Anyway, not long ago shortly after we had started making love she woke up by mounting me one morning. Not gonna lie, took me by surprise. I figured a few days ago I'd wake her up similarly by caressing her and easing into her but I sorta got taken by surprise again when she got to the "I'm awake" stage I got knocked off and told she didn't like it and it felt almost like rape which kinda shocked me and felt a bit like a double standard but I apologized and moved on.

Cut to now, a few days later and she's telling me she enjoyed it and wants it again but for real this time without interrupting with a punch. Now I'm lost. I just don't know, do ladies enjoy being...I mean, forced? I was taught rape is bad, what's going on? Ladies, help?

I am 19 turning 20 in a few months and applying to a bachelor's at a college. I'm weighing the options for a program in another city (Toronto) because it's a better course but I just don't have the money. I had some bad stuff happen in the last while (got my bank account frauded) and I started a new job but with car payments and everything I just make enough to cover everything and I was behind on bill payments by a month for a while. My parents make around 80,000 combined. I'd hope to have some saved up by the time I go but is there some way I can get living expenses supplemented?

I am asking this on my friend's account as I don't have yahoo (nor do I want it).

I work in an office as a content editor and recently a really cute guy started at the cubicle across from me as a content writer. He seemed bad boyish even though he always comes in dress shirts and dress vests, he wears a black leather jacket, has tattoos and messy (but nice) black hair but when people started talking to him he's actually really smart and shy.

I'm a really friendly person so I said hi on his first day and struck up conversations and talked to him often since. He mostly gravitated to me at one of our coworker's retirement party.

A friend of mine said she's jealous cause she wants to **** him and he's obviously crushing on me. She told me he's a virgin that shocked me, he's pretty sexy and 21 (I'm 33) but also shocking cause there are at least two other grown women who have been trying to get into this poor kid's pants. But I've started kind of taking notice of his actions and I think he's crushing on me but he won't do anything. I went for a drink with him and a few coworkers and I kept flirting with him and touching him to try and get something out of him but he'd just look away. He got red faced at one point I touched his leg, is he shy to reciprocate?

Should I be pursuing something with this kid, I mean he's really sweet, but I've had men break my heart already in the last while.

Is it worth it? How would I even get him to reciprocate? He seems like he might be really shy?

I have my car to get me from A (Sudbury) to B (Calgary), a room to rent when I get there just enough to rent it, my bills are paid and I'll have just enough for food and otherwise. If anything happens on the road I'm probably pretty screwed. Let's hope nothing happens.

In a 2006 Buick Allure, I expect it'll cost me around $4-500 (plus a little for food to get there. And I'm taking all my possessions with me.

Am I crazy?

I'm very nervous and afraid. I've never left my city to live somewhere else. But recently I've had some financial woes, I had a lot of money stolen off me by (former) friends not counting what I gave to my family. I'm likely going to be living in Calgary in my car for at least a week or so and I am very nervous. Any advice?

I'm a 19-year-old man who's always dreamed of meeting and being swept off his feet by a wonderful woman (and vice-versa, equal effort right?) and I've put in some effort to date. But I've just never found anyone and never done anything with anyone. At nearly 20, I feel like I'm just wasting time now. But I think I have to be okay with being single first.

Doesn't help that I may or may not have feelings for my best friend but she's in a relationship, I dunno. I wouldn't know love if it came up and punched me square in the jaw.

I have always been afraid of ending up all alone. How do you be okay with being alone?

I have a history of anxiety and have been feeling very jittery and strange lately. Like everything (especially senses) is numb and I don't want to go anywhere or do anything aside from sleeping. My memory has also become cloudy and I've had headaches on and off. I'm not sure what's wrong. At first I thought sleep deprivation and took pills for it but now I'm worried it's anxiety or something else (I'll admit, I tried weed a week ago and that's about how long this has been going on). I want to go to the doctor but I'm just afraid that there won't be anything to be done. Anyone have any suggestions?

I'm 20, soon to be 21. I just started college and I have had no sexual experience period. I had my first kiss when I was fourteen. But that's about it, I haven't even dated since then. It's not that I've been saving myself for marriage or anything, I'm just really shy and nervous around people and sex has always been something that kinda scares me. Maybe has a bit to do with a female friend sexually assaulting me when I was younger but sex is something that's always been special to me. Not to mention, I'm terrified if I let her do this she might just end up leaving me soon anyway.

My girlfriend is 24 and a very experienced woman who enjoys sex. She's been patient over the four months we've dated and I don't want to deprive her of something she needs but at the same time it's intimidating knowing she's dated two guys before me and been with a few besides that (no, she's not a slut).

Please help. How do I get past all this? She's been very understanding and patient so far and just really started encouraging me in the last while. What do I do?

I was fourteen when I met her. Let's call her Mrs. Howell. She's beautiful and smart and kind and really fun to be around. She was my English teacher for grade nine and History for grade ten. We struck up a friendship and I'd drop by at lunch or after school to talk for a while and let her read some of the stuff I'd written (I really like writing) and discuss literature and stuff. She left to England some time ago but she's coming back for the summer. I've messaged her a couple times since she left. But I can't help but get the idea out of my head that I should pursue a relationship with her should she return. I really enjoy her company and I am 18 now and will be out of school by the time she returns. I'm not the boy that I was when I first met her, I'm a grown man who can make his own decisions. But I'm just not sure if or even how I should do this. Is this morally wrong? Would someone ever consider this? Has anyone else had this situation? How should I go about this if I do?

I was fourteen when I met her. Let's call her Mrs. Howell. She's beautiful and smart and kind and really fun to be around. She was my English teacher for grade nine and History for grade ten. We struck up a friendship and I'd drop by at lunch or after school to talk for a while and let her read some of the stuff I'd written (I really like writing) and discuss literature and stuff. She left to England some time ago but she's coming back for the summer. I've messaged her a couple times since she left. But I can't help but get the idea out of my head that I should pursue a relationship with her should she return. I really enjoy her company and I am 18 now and will be out of school by the time she returns. I'm not the boy that I was when I first met her, I'm a grown man who can make his own decisions. But I'm just not sure if or even how I should do this. Is this morally wrong? Would someone ever consider this? Has anyone else had this situation? How should I go about this if I do?

Pretty self explanatory question. I'm seventeen and having a tough time finding a job. I intend to take English as a course in College and getting hired on a publishing company in Toronto is pretty much my plan.

Are there any ways to find someone with a punk tomboy kind of personality?

I've tried dating sites but those damn things are useless. I'm beginning to think I'll be alone forever :S

Question is fairly straight-forward, but first, a little backstory: I was born in a small town in 1997, am sixteen, was bullied for quite a few years up until the last two years. My parents divorced about two-and-a-half years ago when I was around thirteen and my brother left to get away from it. At the same time a close friend died, and now that my brother is back and bitter about coming back, he is taking it out on me.

I'm tired of feeling like I don't fit in, even among family. I guess maybe I do need a therapist but for now yahoo is good enough.

A big part of me remembers Alysa, remembers how kind and caring she was, and yet she is gone. How can I pretend to look forward to the future knowing that?