“Should I Date the Broke Guy With No Teeth?”

When I was 15, my brother was friends with a guy named John who was very handsome but slightly conceited. He even hurt my feelings on a number of occasions. Eventually, he developed a crush on me, but I never went out with him. Now I’m 32 years old and I noticed him on a family member’s Facebook page, so I sent him a message. At the age of 35, he is homeless, has no teeth due to cocaine use, but seems nice. He says he’s been clean over a month and wants to get his life together so I can be with him. Only problem is, how could I be with…

“Does My High School Teacher Want to Date Me?”

I’m 22 and just graduated from college. Recently, I’ve been in touch with a teacher (in his early 30s) from my high school. We always had a good relationship and have gotten lunch a couple times in the past but we’ve definitely moved past that. We got dinner one Friday night, he picked me up and paid. I took him to a baseball game with a couple of my friends, and he in turn brought me to a baseball game with some of his. We’ve been texting regularly and last week I went to his house to watch the various sporting events that were happening and we ended up snuggling on the…

Your Turn: “Any Advice for Meeting the Family?”

In a feature I call “Your Turn,” in which you, the readers, get to answer the question, I’m presenting the following letter without commentary from me: I’ve been dating my girlfriend for five months now. She met my family very early on in our relationship and she gets along with them great. (My family’s pretty wonderful and they were very friendly to her.) But I’ve never met her family. (They live on the other side of the country.) So here’s the thing: I’m going with her to her home state for a two week visit in August. During this time, I will be staying at her dad’s house for a while, visiting…

“My Boyfriend Treats His Mom Like Crap”

I recently moved in with my boyfriend of 8.5 years. We live in his home town and his mother lives just a few blocks away. We frequently stay for dinner at her house, along with his siblings. His mother is a stay-at-home mom who will literally do anything for her children, which I respect very much. Although I focus on my career, I can see the tremendous work she does around the house and the hours she puts in keeping the younger siblings of my boyfriend happy, fed and loved. However, my boyfriend and his brothers are indifferent to her hard work. They frequently make rude comments, stressing her out, and do…

“I Can’t Stop Men From Falling in Love with Me”

I am 23 years old and a computer science major so naturally I spend a lot of time around men. This is great. I have a tight bond with the few women who also study in my year, but I am also excessively fond of crude jokes and beer and I get along well with a lot of the men here. I had some really awkward teenage years and I am finally learning to appreciate and love myself. I am very positive and outgoing and I know this is what attracts a lot of men. I dress “prettily”; I like dresses and since I recently lost some weight I’m just enjoying experimenting…

“My Ex’s New Girlfriend is Bad-Mouthing Me”

I have a 12-year-old daughter, Betsy, from my first marriage. My ex and I split custody 50-50 with no child support, etc. We divorced over five years ago after a 10-year marriage. We married young, never really got along and argued constantly. It ended up being a surprisingly amicable divorce. The problem is my ex’s girlfriend, “Brandy” (they have been dating about 1 1/2 years and live together). On the few occasions that I have talked to her, we had gotten along fine and had some nice conversations. So a few weeks ago I asked if she’d like to join me and Betsy to go shopping for a dress for her first…

Your Turn: “My Boyfriend Isn’t Ready to Be My Daughter’s Dad”

In a feature I call “Your Turn,” in which you, the readers, get to answer the question, I’m presenting the following letter without commentary from me: I have a three-year-old daughter. The father is not in her life at all. The father’s family is not in her life at all. I was dating this guy named “Carl” for a year who was a wonderful guy for my daughter but not for me, so we split up. The day I split up with Carl I met a guy named “Frank” whom I have been dating almost two years now. I was living at my mom’s and he was living with his friends for…

“He Has a Girlfriend. Should I Confess My Feelings Anyway?”

New readers, welcome to Dear Wendy, a relationship advice blog. 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), or submit a question for advice. I like a guy who has a girlfriend. He’s someone I have known for a couple of years who has only become my friend over the last few months. He had to move away for work, so I don’t see him frequently, but when I do, he seems happy to see me, smiling at me and giving me hugs. He is naturally charismatic and outgoing, and he has a…

“He Said He Doesn’t Love Me”

It’s time again for Shortcuts. For every question, I’ll give my advice in three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss when it’s way, way, way time to MOA, and letting a friend know you don’t share the same fantasy.

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