Dear Miles: “I Wish I’d Ended Up with My College Boyfriend”

Today is a very special day in the Condellberry household — Miles turns 10! It was just under four years ago, when Miles was six and I was eight months pregnant with Jackson, that Miles suddenly — like over the course of a few hours — got very sick (from complications of his just-diagnosed diabetes) and almost died. But he beat the odds and survived, and we count every day with him since as a gift. We love him so much. Those of you who have been reading the site since the beginning probably remember the wise and surprisingly philosophical advice Miles has shared in the past through his guest column, Dear…

“My Boyfriend Changed His Mind About Moving in Together”

Around six months ago I graduated from college. Since then most of my friends have moved away, and I have yet to find a secure job. It’s been tough and it has affected my relationship with my boyfriend. We started dating almost a year ago, and then, around a month ago, I broke down a bit from the stress of post-grad life and growing insecurities and we broke up. We recently got back together because he said he had made a mistake and that I was “the one.” Things resumed rockily at first but are going very well now. That is, until yesterday when I asked him if he still thought we…

“My Boyfriend and I Don’t Know How to Argue”

I’ve been in a relationship for a year with this great guy with whom I have great chemistry and feel so in love with. The only thing that bothers me is how we argue. I get annoyed at a lot of little things and I am aware of how taxing it can be to another person. Although I try not to verbalize my annoyance, my boyfriend can tell how I’m feeling, will make me explain why I’m upset, and then will get angry and defensive. A recent example: He was texting someone while we were hanging out, but it was just one text to someone he hasn’t spoken to in a while….

“My Fiancé Can’t Provide For Me. Should I Still Marry Him?”

I’m engaged to be married in eight weeks but am beginning to have cold feet. My fiancé treats me like a true queen, but he can’t provide for me the way a husband should because of his finances. I’m a school teacher making $34,000 a year and my fiancé currently works at a warehouse job making about $12 an hour. He also has a six-year-old son whom he has joint custody of and pays child support for, which leaves him with a small paycheck. We split all our bills and sometimes he asks me for some money here and there to carry him to the next pay period until I barely have…

Shortcuts: “Oops, I Accidentally Showed My Husband’s Friend a Revealing Photo of Me”

New readers, welcome to Dear Wendy, a relationship advice blog. Read some of the most popular Dear Wendy posts here. If you don’t find the info you need in this column, please visit the Dear Wendy archives or the forums (you can even start your own thread), do a search in the search bar, or submit a question for advice at wendy(AT)dearwendy.com. It’s time again for Shortcuts. For every question, I’ll give my advice in just a few sentences because sometimes the answer to a person’s question is so obvious and the need to hear it so great that being as clear and frank as possible is simply the best way to…

“My Boyfriend Doesn’t Know About My Husband”

I’m having an affair that my husband knows about; the problem is my boyfriend doesn’t know about my husband because we live a few cities away, and it’s getting complicated. It all started three years ago. My husband and I had money issues, kid issues, boredom issues. I felt crushed by the stress of a youngest child who had disorders, was labeled special needs, and needed my care on a constant basis. One night I was invited to a party where I met Jim. Jim was smooth and nice and caring and so care-free — the exact opposite of my own life. We fell in love, and he has no idea that, after…

“My Boyfriend’s Family Thinks He’s a Thief”

Earlier this year my boyfriend’s father committed suicide. At the time, “Jake” and I had been together about a year. Jake’s parents divorced a few years ago and his father’s family likes to blame Jake’s mother – they claim he never got over her — for the suicide even though his father remarried in October of 2014. I guess getting remarried to a woman they all love counts for nothing?! One of the most difficult things – more difficult than dealing with the death – has been how Jake’s family has betrayed him. Jake entered the military in 2003 after graduating high school, and they seem to be angry at him for…

“I Don’t Like How My Husband Throws a Party”

My husband and I had about nine friends (a mix of my pals and his) over to play board games/poker/card games on a recent Saturday night. I thought the food and drinks should be set out ahead of time and arranged for a party atmosphere, but my husband wanted to pile up a bunch of bags and put stuff in the fridge and let people forage (or go fetch it for them throughout the night). I didn’t want to end up doing all the work, so this devolved into a fight in which I had to cool off by going away for an hour (fortunately, only one person arrived for the party…

Morning Quickie: “I Don’t Want to Sleep With My Fiancé”

My fiancé and I have been struggling recently with the whole sexual part of our relationship. I’ve had a really bad experience in the past that also happened to be my first time, and I am still getting flashbacks. Not to mention, I have zero desire. Also, I don’t approve of his watching porn. I’m overweight, and for him to look at naked girls and get pleasure out of it is cheating to me. Also, back to the experience before: That guy used to always have the Playboy channel on, which also contributes to flashbacks for me. I hate it. I want to help him out and not make him feel bad…

“Should We Let Our Teen Daughter Sleep With Her Boyfriend in Our Home?”

My live-in girlfriend’s 15-year old daughter, “Jill,” has recently become sexually active with her boyfriend of six months. Luckily, my girlfriend is a realistic parent, and her daughter is on birth control and my girlfriend didn’t overreact. She realizes that you can’t stop raging teenage hormones, and that it is better to be aware than live with your head in the sand. Besides, my girlfriend is actually my teenage sweetheart (reunited after 25 years apart), and she and I were having sex at the same age 29 years ago (man, I am old), so we are trying to fight any hypocrisy. We did get worried about the frequency of the sex, and…

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