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The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He’s been on more dates than you can shake a lengthy bar tab at, and he’s here to help the average guy step his dating game up a notch -- or several. The Question Hi Dating Nerd, Things are going great. I recently reconnected with a girl I had a huge crush on in college, and for some reason she’s into me now, and we’ve gone out a few times, and it’s been amazing. We’re really connecting. But there’s a major problem. She used to be a huge party girl -- like, she drank a lot, and she slept with lots of people. This really bothers me. I don’t like thinking about her having sex with other men. And it also makes me doubt whether she’s ready for a serious relationship, which is what I want. What do I do about this? - Jealous Jack The Answer Hi Jealous Jack, What do you do? Well, the sho...

Here we are, entering the holiday season, which means scrambling for gifts. But even before you’re compelled to suffer on a checkout line so deep you can’t see the front, or prior to starting that spreadsheet to compare the best bargain buys on the internet, you’ve got to figure out what the hell you’re getting -- particularly for that special person in your life. Luckily, former Miss Universe Olivia Culpo has the answer: just get her everything. OK, not exactly but pay attention fellas, the 25 year-old model is giving up the cheat code for winning the holidays with your partner. “You can do something like the 12 gifts of Christmas,” she said. “On Christmas Day you have 12 gifts that you put together and you mark every one and it’s really sweet.” Sure, that sounds expensive, right? But it does not have to be. Like the saying goes, it’s really the thought that counts. “It can be simple or it can be really extravagant,...

The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He’s been on more dates than you can shake a lengthy bar tab at, and he’s here to help the average guy step his dating game up a notch -- or several. The Question Hi Dating Nerd, I’m noticing that a lot of my male friends, at one point or another, have been cheated on. It makes me really afraid of the idea of a committed relationship. And it makes me think that women are just okay with cheating. So I wanted to know, like, do women feel bad when they cheat? - Suspicious Stan The Answer Hi Stan, Let me begin this by saying that your question is a little silly. Of course, women do feel bad when they engage in cheating behavior . (Sometimes not, in some cases, but I’ll get to that in a second.) This is because women are people. There’s really no reason for the gender specificity in this question. Sure, men a...

In books and TV and movies, first kisses are presented as glorious things. The characters always seem to know the exact right time to kiss their date . The protagonist leans in, their date leans in -- their lips meet. And it always seems to be happening in some picturesque setting -- maybe in a rustic garden, with a light snowfall and swelling piano chords in the background. Alas, reality is much more awkward and inorganic. There's no way to know for sure when someone wants to be kissed, so it's best to ask. That being said, asking can be scary and uncomfortable, even under the best of circumstances! There's no precise formula, but here are some ways to make the process as smooth as possible, and to ensure that she texts all her girlfriends the next day about how great that first kiss was. 1. Timing, Timing, Timing The golden rule is to ask for a kiss when she's as relaxed as possible. That classic opportunity -- the end of a date, whether is the first date or a later ...

The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He’s been on more dates than you can shake a lengthy bar tab at, and he’s here to help the average guy step his dating game up a notch -- or several. The Question Hi Dating Nerd, I’m kind of in love with one of my best friends. And I think it’s possible that she feels the same way about me. Initially, things didn’t seem romantic, but the energy between us has changed over time. And I’m wondering: do you think it’s a good idea to pursue a friend? Do you think that can lead to a good relationship? - Amorous Alex The Answer Hi Alex, So I have a suspicion about this letter of yours. I’m guessing that what you want me to say is “yes.” That you should absolutely throw yourself at this girl, that the length of your friendship is no obstacle, that the desire in your noble, manly hea...

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At some point or another, we are all tempted by the fruit of another. It’s an inevitable part of human nature, especially when curiosity, boredom or monotony gets the best of our hearts -- and, ahem, our groins. That being said, if you commit infidelity in your long-term relationship and fess up to your wanderings, could your union actually be better off than it was before you strayed? According to several psychologists, the answer is a resounding: nope, not at all. As psychotherapist and author Dr. Jenn Mann explains, when it comes to trust, cheating is like a bomb that goes off between your twosome. “It destroys this core foundation that is needed for a successful relationship. The desire to have our beloved partner to ourselves is such a primal need that the breach of a monogamy can inspire a level of hurt and rage that is unique to other kinds of betrayal,” she explains. Before you move in the direction of your disloyal ambitions, consider the consequences it cou...