DEAR NATALIE: I slept with this guy on the first date. Not my proudest moment; I got pretty drunk at the bar when we went out the other night and stumbled back to my place. You know the rest. Anyway, ... more

DEAR NATALIE: I have reconnected with my old boyfriend from college after 20-plus years. During that time, we both married. He is divorced and has two kids that are in college now. I married and lost... more

DEAR NATALIE: I’m afraid I’m becoming bitter towards relationships. I’ve been single for a while now and having a much harder time dating in my early 40s than I did in my 20s or 30s. I was married and... more

DEAR NATALIE: My best friend has been in a bad relationship for years now and no one understands why she stays in it. He treats her poorly, is rude to her in front of her friends and can be very contr... more

DEAR NATALIE: I started dating this guy recently and he likes to send me DMs on Instagram throughout the day with funny memes to look at. Well, the last two have not been funny. He found these videos ... more

DEAR NATALIE: I have a close circle of friends. Well, I thought they were close. Recently, my one friend got engaged and some of my friends threw her an engagement party but I wasn't on the list. I fo... more

DEAR NATALIE: I have been friends with “Shawn” for years and we have always had a good relationship. Granted, he deals with some mental health stuff that can make him challenging to be around, but ove... more

DEAR NATALIE: I have been having an affair for about three years with a married man from my office and I am sick of the mind games he has been playing with me. He always talks to me about leaving his ... more

DEAR NATALIE: I am 24-years-old and have never really been in a relationship before. The idea of sex always made me nervous and while I have kissed a few boys, it has never gone beyond that. I just st... more

DEAR NATALIE: My mom’s new boyfriend is disgusting. I was at her home for dinner the other night and he had been drinking beer and started commenting on how hot I was -- in front of my mother. She tri... more

DEAR NATALIE: We recently had to put my dog down. It was incredibly sad. I had my dog, Sadie, for almost 12 years and she was a huge part of my life. My whole family was incredibly supportive of me ex... more

DEAR NATALIE: I am engaged to an older man who I have been dating for the past few years. I have moved some of my clothing and other personal items from my house into an unused room in his house. He h... more

DEAR NATALIE: A few years ago, I hosted a birthday party for my husband at a nice restaurant and invited his four kids, their spouses, and their 9 grown grandchildren; all of whom are heavy drinkers a... more