Tag Archives: dating

Dear Wendy Updates: “Lost In Translation” Responds

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing today. After the jump, we hear from “Lost In Translation,” a 26-year-old woman whose language exchange IM buddy from France was planning to make a special trip to Calgary to see her while he was in Toronto for a wedding. “I know he’s not rich, and he doesn’t seem to be coming to Calgary for any other reason. I’m hard-pressed to believe that someone would go that far out of his way just for a short platonic meeting. What is he really expecting of me? Should I ask my boyfriend to join us?” She wrote. After the jump, find out if she went through with seeing him. Keep reading »

Dear Wendy: “When’s The Best Time To Discuss STDs?”

After getting dumped by my boyfriend of five years (and some time to get over that), I’ve recently re-entered the dating world. So far it’s a lot like I remember it to be; however, the only difference is that this time I’m not a virgin, and neither are most of the people I’ve been out with. And while I’m not quite ready to leap into bed with anyone, I’m becoming increasingly confused about the appropriate time to broach the subject of getting tested for STDs. Is there a way to bring up the topic without being offensive? I feel like I’m being a bit of a prude here, but after working for a college health center for a few years, and seeing the damage that STDs can do, I’m just not interested in putting my health at risk, even in the name of love. — Cleared for Takeoff

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Dear Wendy: “My Girlfriend Lets Her Friends Take Advantage Of Her”

I’ve been with my girlfriend for about two and a half years. The one problem I have is with my girlfriend’s friends and how they handle money. From everything I know, everyone is on pretty similar pay levels, but her friends always seem to be short on cash when they do stuff together. My girlfriend always covers everything, whether it’s drinks, dinners, or tickets to events, and gets defensive when I ask about it and says “it’s just a couple dollars between friends.” Recently, I’ve been getting short-changed by them, too. They will invite us out to a fancy restaurant, order up a storm of appetizers and bottles of wine, while I’m content with my single entrée and beverage, and then when the bill comes, they’ll suggest we split everything evenly, and then when it comes time to pay, what they’ve put in is about half of what their evenly divided portion should have been. I’ll offer to pay the remainder to avoid an issue, but it leaves me peeved. I can cover these financial indiscretions without problem since I’m better off financially than most in the group, but my girlfriend is saving up for a big trip soon, and can never seem to get out of debt, yet is still always paying for her friends and is mortally embarrassed when I threaten to call them out on it. Also, if I’m thinking about a long-term future with her, I’m afraid to have joint finances if she can’t seem to manage her own. — Need a Bail Out

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10 Subtle Ways To Make The First Move

Happy Sadie Hawkins Day! Sadly, I never attended any of the Sadie Hawkins dances in high school. Why? I am a complete failure at asking guys out … and I had no game back in high school. But I digress. Anyhow, what I have become a total winner at is dropping subtle hints to let a guy know I’m interested. If he takes the bait, then I know he’s down. After the jump, some foolproof tips for making the first move this Sadie Hawkins Day. Keep reading »

Sex With Steph: Medical Issues Are Affecting My Love Life

I am a 21-year-old young woman, not dating anyone at the moment. I also happen to have a plethora of medical issues, Even though I’ve worked hard my whole life not to let my medical issues get in the way of living my life, there are some situations where it’s unavoidable. Due to a medical misjudgment when I was 5, I am unable to have “conventional sex.”

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Dear Wendy: “My Guy Friend Wants To Sleep With Me”

It’s time again for “Shortcuts.” For every question, I’ll give my advice in three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss guy friends who want to take things to the next level, mercy-killing a relationship, and guilt over being “the other woman.” Keep reading »

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