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When an Ex Comes to Town

I have been seeing this guy for a couple months now and have known him for a little over a year. It turns out we had been mutually interested in one another for quite some time, but due to our professional relationshi…
I'm Dating an Older Man With a Daughter

This post has been submitted anonymously by a Datingish reader. I've been dating this guy for almost two years. I'm 26 and he's 40 and has a 19-year-old daughter. He's been married three times prior to me. The daughter…
Re-Entering the Dating Scene When You Have Kids

I am 30 years old, unmarried, with a 2-year-old daughter. I was at one point engaged to her father who I'd known since college, but we ended up calling it off after we realized we'd rushed into a romantic relationship…
Going With the Flow

So here's the story: I've been out of a relationship for around seven months and let me tell you that I am not desperate or actually looking for anything. Though recently, I've noticed myself unintentionally talking to…
I'm Dating My Friend's Ex

My friend met a guy on an Internet dating website before Christmas. They seemed to hit it off and when she showed me photos, I thought he looked familiar but didn't take any notice and went along with my life as normal.…
Friends with Benefits, Now with Kids

I have a dilemma, and it's stereotypical and cliché and something I know everyone will tell me to get out of unless I want my heart broken. I'm having a friends with benefits relationship with someone right now…
When Do the Condoms Come Off?

I was completely baffled about a month ago when I was having a conversation with one of my best guy friends. We had gotten on the subject of our recent sexual partners and then on the subject of contraception. I was in…
Dating Someone With a Mental Illness

John had a lot of problems. But so did I. And we were crazy about each other. I was nineteen and had been living on my own for six months. John and I had been friends since we were sixteen, and I had just moved to the…
Creepy or Cute?

My friend Amelie met this guy Jack, who is from Scotland, about a year ago. A few months after they met he left the United States and returned back to the UK. Since then they often Skype and write emails, and she has ev…
Finding a Good One (for You)

There seems to have been a lot of posts on Datingish lately about what is and is not appropriate in a relationship. Ultimately, reading the posts and comments has been incredibly frustrating for me, because I think the…