Shortcuts: “Does My Cross-dressing Fiancé Want to Be a Woman?”

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 go.   Is there a way to figure out if my cross-dressing fiancé wants to become a woman? I love him but need a male. Can you help? I think he wants to be a lesbian. I like his penis. — Needs a Man

Your Turn: “My Married Boyfriend Won’t Leave His Wife For Me”

I feel so desperate, depressed and lost. For a few years I have been in a relationship with a married man, who was initially my advisor at the university. I don’t excuse myself and I know most people would judge me very harshly, and I do too. The guilt that I feel has brought me to dark places I never imagined existed in me. I know the way things happened is wrong, no matter how much love there is. I felt powerless, drowning into something much bigger than me, that was already destroying my self worth. Being in this situation has crushed my self-esteem and sense of worth. I’m drowning, this is…

“Should I Tell My Wife I Hired Escorts After We Married?”

I, like a previous LW have used escorts. The difference is that I am married. I got married in 2008 and love my wife, but I never had sex with anyone else before her and did not have much sexual experience. We are close, but she always looks at sex as a chore and we never discuss it, or I couldn’t dare tell her I masturbate. I never even heard of escorts until 2010 and could not believe they were operating in my general area. After eventually building up the courage, I visited one; she was very thoughtful and nice, I was very shy, and she guided me through it. To cut…

Quickies: “Should I Spend New Year’s Eve with My Friends or My Boyfriend?”

For New Year’s Eve my friends and I want to go to a party so we can dance and have fun, but my boyfriend wants me to spend it with him and his friends at his home, which I think is kind of boring because, instead of dancing, we will be drinking and I don’t know his friends that well. I tried to convince him to come with me (my friends want that too) and he said he will but he will not have fun because it’s not his kind of party and, of course, that will make me feel bad. He was also saying that it would be better if we…

“How Should I Deal With Racist Family on Thanksgiving?”

Do you have tips (or a guide) to surviving Thanksgiving with racist in-laws/relatives? Is it all about the extra glass of wine, or is there ever an appropriate time to pipe up? Thanksgiving this year is at my and my husband’s home, and I’m wondering if I can set polite boundaries to casual and frequent racist remarks without making it awkward in the future… — No Racism Please

“I Desperately Want Another Baby But My Husband Does Not”

My husband and I have been married for several years now. He wasn’t sure he wanted kids when we first started dating, but by the time we got married he said he thought he would probably agree to them at some point. I was pretty sure I wanted at least one, but not 100% sure. We had (and still have) a great relationship, so I figured we’d work it out–and we got married. About two years ago, he said he was ready to have a baby. I was too, so I was delighted. We agreed that we would only have one. We discussed it and thought that would best fit our lifestyle,…

“I’m Tired of Supporting My Boyfriend”

I have been dating my boyfriend for 3-1/2 years and we have a 2-year-old daughter together. For the entirety of our relationship we have split the bills – first three ways with our old roommate and now just two ways since she moved out two years ago. We split the rent, power, phone, cable, and internet, as well as the car payment and insurance (we share my car). He has been working the same job since our daughter was born and only brings home a little over $1700 a month after taxes while I bring home about $2700 a month after taxes. I have many more bills to pay such as credit…

“My Fiancé Wants to Buy His Mother’s House But I Don’t”

My fiancé, “Dan,” (28) and I (24) have been together nearly three years. Before we met he moved in with his mom to help her out after her divorce. I also live with my single mother as I was broke after college. Now his mom is talking about selling her house and my fiancé has every intention of buying it. He wants me to move in and I do not want to live there under any circumstance, especially considering he intends to co-buy it with his brother (30) and his brother’s girlfriend. His mother also has no plans for after she sells, and she has even suggested she just stay and rent…

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