Dear Wendy: “I’m 22 And He’s 35. Can It Work?”

This weekend is an all “Shortcuts” weekend for Dear Wendy. For every question, I’ll give my advice in two 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 May-December romances, talking smack on Facebook, loving on a deadline, and undeniable cheating signs.

Wendy, I’m 22 years old and currently seeing a 35-year-old man who is WAY beyond successful. I think he is looking for a serious relationship but I’m not sure if he wants it with me. My friends think I’m arm candy but when I’m with “35″ we get along great and have set dates for vacations, parties etc. Am I setting myself up for heartbreak? — Young One

You’re only setting yourself up for heartbreak if you believe a relationship consists only of “vacations, parties, etc.,” and you aren’t emotionally prepared to handle the inevitable challenges all couples face, despite their age differences.

I am a 21-year-old girl that just broke up with my 23-year-old boyfriend of more than three years. He was broke and refused to get any sort of job for over a year, he lived with his parents, didn’t have a degree, and never EVER wanted to go out, so I dumped him. Since then, he and his friends have basically been badmouthing me online via Facebook, calling me fat (I am a slim size 4 and go to the gym for two hours a day!), blaming me for his problems, and treating me like crap. He is the one that screwed up and stopped putting forth any sort of effort in the relationship. I am trying to decide to unfriend him on Facebook. Is it a good idea? — Formerly Friendly

Yes, good idea. And while you’re at it, drop all his loser friends, too.

I met the most wonderful man about seven months ago. He’s 26 and I’m 25. I’m not exactly ready to settle down right now, but I am obviously very interested in moving towards that course. My guy, on the other hand, just got out of the military and wants to go back to school three hours away and doesn’t want to enter into a long-distance relationship. I realize that there’s no way we could even work out a long-distance thing if he already has a negative attitude towards it. Therefore, I have one year before this relationship hits its deadline and I’m already devastated thinking about the inevitable. Should I just enjoy the relationship for the next year? Or do I end it now, with the mindset that I’m still waiting for him to leave? — Waiting for the deadline

Ask yourself what you’ll regret more: missing out on what could potentially be a wonderful year together — and perhaps giving you a stronger base on which to build a lasting relationship in the future — or prolonging the broken heart you’ve already said you’re going to have one way or another. Only you can make this decision.

I have been in a relationship with my guy for five years. During the first two years of our relationship he was out all times of the night and went out every weekend with his friends and I started getting suspicious. Our sex life also changed and he blamed it on working late hours. I found a phone number in his phone and got a gut feeling about it. I called it and some girl picked up and told me they were just friends. I looked up the phone bill and realized he had been texting her almost every day for two months. When I confronted him about it, he claimed they were just friends and nothing happened. Two months later I found another number. I called, and this girl told me he tried picking her up at a gas station. At first he denied it and then told me he did do it but had no intention of following up on it — he was just acting up in front of his friends. Then, I bumped into the first girl at a bar one night and she approached me and told me they had slept together and she had lied about them being only friends. My boyfriend insists that’s a lie and to this day (three years later) he claims he never cheated on me and is just guilty of flirting. I love him and I want to trust him, but something tells me he isn’t telling me the entire truth. Should I let the past go or should I follow my gut instinct that my guy is a cheater? — Desperate and Confused

I’m not even gonna touch this one. “Something” tells me the readers will have plenty to say about this in the comments.

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*If you have a relationship/dating question I can help answer, send me your letters at {encode=”dearwendy@thefrisky.com” title=”dearwendy@thefrisky.com”}.

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