5 Questions You NEED To Ask on a First Date

Ah, the awkwardness of the first date. There’s nothing quite like it. At least in a job interview (where the awkwardness is about equal), it’s acceptable for the employer to ask questions designed to root out crazies.  Yet on a first date, where the ‘candidate’ stands to wreak more havoc than any other person in…

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Lady Chastity

Dear Dr. Darcy: 

My ex-boyfriend was quite kinky and was always introducing new things to the relationship. I wasn’t all the way into it but went along with it to make him happy. As part of a “cuckolding” and “male chastity” scene, he introduced me to my current girlfriend. The scene was hotter than I expected and we hit if off. I stayed in touch with her and things progressed to the point where I ended things with my ex-bf and started dating her.

Now the twist. My ex was so sad and devastated from the break up that he wanted to stay friends, like to actually spend time with me. I felt bad for him but I wanted to be fair to my new girl. So… um… I made him a deal. If he stayed locked in his chastity cage with me keeping the keys then we could hang as friends. The moment he took it off would be done forever.

I thought he would last a week or two and we’d part ways. Instead it was almost a month before he finally begged to be unlocked. By that time I was enjoying our platonic relationship and even sorta getting off on being his “keyholder” and teasing him. Is this fair?

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The Importance of the First Kiss

Dear Dr. Darcy:

I’m a man in my early 30’s looking for a relationship. Back in college I had a really bad experience and I think it’s interfering with me finding a woman today. What happened was I hooked up with a girl one night after a party and the next day she told me she didn’t want to see me anymore because there wasn’t chemistry. Later that day my fraternity brothers told me that she told all her sorority sisters that I was an awful kisser. Ever since then I have awful thoughts floating in my head when I’m about to lean in for the first kiss. I’m convinced that the sorority girl is right and that I must suck as a kisser and not surprisingly I rarely get past the first kiss with a woman. How important is the first kiss? Is there a general way that women like to be kissed? Or maybe some common mistakes you can point out to me that guys make when kissing? Please help a brother out.

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9 Things Happy People Do That You Don’t

Happiness, it turns out, is a 50/50 roll of the genetic dice: Half of us are born with a predisposition for it.  Those who aren’t are left with a choice: Do you want to live your life grumpy and pessimistic, predisposed to anxiety and depression, or do you want to adopt the specific ways that happy people think and act, which, when followed, absolutely makes up for the hereditary piece. 

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When Is Enough Enough?

Dr. Darcy, I’m a 40-year old woman who fell in love with a woman for the first time. It is like nothing I have ever experienced. But I have a problem with her talking and hanging out with her ex, who she admits still has feelings for her. She even told me they hung out one night and watched a movie. It was late so her ex slept on the couch (later I found out that she slept in her bed fully clothed but NOTHING happened…hard to believe right?) [My girlfriend] is 48, her ex is 28 – BIG difference in age but the 28 year old knows how to play mind games. My girlfriend suffers from mental illnesses such as BPD [borderline personality disorder], anxiety & PTSD. 

 

Question is when is enough ENOUGH??! I’m confused beyond belief as to what to believe anymore. My girlfriend says she is just a friend – they’ve known each other for 2 years but only dated 3 months). Never had sex with her but being new to the girlfriend/girlfriend situation, I thought exploring with your fingers and kissing were sex?? I feel as though I can’t break up with her but I can’t stand feeling like this anymore…

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The Lesbian Bridesmaid

Dear Dr. Darcy: I have 3 daughters, the middle daughter (straight) is getting married, and youngest daughter (gay) was asked to be in bridal party.  The 2 sisters are having a fight because the bride wants sister to wear a… dress (the gay daughter NEVER wears a dress), and, as a result, the gay sister…

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