How Do I Know When the Relationship’s Worth Fighting For?

Ryan O’Connell tackles big relationship questions, from how to know when it’s time to let go, to what to do when you like different things in bed.

The Strip Club DJ Who’s ‘Terrible With Women’

Ryan O’Connell tells you how to deal with insecurities, wanting more from your relationship, what to do when you’re in a rut, and more!

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What to do When You’re in Love With Your Best Friend

Ryan O’Connell tells you how to deal with rejection from your best friend, which sex habits are acceptable, the ins and outs of being a cougar, and more.

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How to Lose Your V-Card as Gracefully as Possible

In this week’s “Call Your Boyfriend” Ryan O’Connell tackles the age-old issue, as well as what to do with your relationship if you get a great job offer in another city.

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No, You’re Not Pathetic If You Reach Out to an Ex

Ryan O’Connell helps sort out the right way to reaching out to an ex post-break up and deciphers the politics of office romances.

I Love You

The Foolproof Guide to Ending a Dry Spell

Haven’t had sex in multiple forevers? Ryan O’Connell comes to your rescue. Also: the politics of first dates, and when to say “I love you.”

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Here’s Why You’re Allowed to Say Your Friend Can’t Date Your Ex

In this week’s “Call Your Boyfriend” column, Ryan O’Connell addresses his concerns with doing drugs while in a relationship and how to handle the age-old conundrum of friends dating exes.

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The Best Music to Have Sex to

In this week’s “Call Your Boyfriend” column, Ryan O’Connell shares his Foolproof Sex Mix, and addresses a question about a particular kind of job. (Very particular.)

Here Is Where We Get Honest About Whether He Likes You

In this week’s “Call Your Boyfriend” column, Ryan O’Connell tackles the incredible importance of honesty and communication, regardless of relationship status. Talk, people!

How to Know If You Are Actually ‘On a Date’

In this week’s “Call Your Boyfriend” column, Ryan O’Connell tackles the delicate line between just “hanging out” and actually being on a date. Related dilemma: he asks you out on a date, then happens to mention that he has a girlfriend.