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 sugar babies, crushing on the bossman, and getting “closure.”
I am in a committed relationship with my boyfriend but at the same time I’m thinking about having a sugar daddy to help me out financially. Obviously, if I have a sugar daddy, it would have to be completely discreet, but at the same time isn’t that cheating? If I did have a sugar daddy, should I tell my boyfriend? Or what’s done behind one closed door shouldn’t be surfaced through to another? Am I crazy to seek out a sugar daddy that could help me out? – Confused Sugar Baby
Yes, prostituting yourself out while in a serious relationship with a guy who is unaware of your extracurricular activities is, indeed, cheating. How about maybe getting a job waiting tables?
I work in a large office and the problem is I really, really like my boss. We are both single and around the same age (early 30s). He’s cute and smart and interesting… just overall great. He’s always joking with me, and I know he is looking for a girlfriend. If he were a normal coworker, I would ask him out in a minute. However, as my boss, he reviews me and determines my ratings. I am pretty sure there is no way we can date while he’s my boss, and I feel like even if I switched teams, it would look weird to start dating someone who had managed me. Is there any way this could work out? Or should I just give this up? I know there are a lot of other men out there, but honestly I haven’t met many as great as he is. — Crushing on the Boss
If you’re able to switch teams relatively easily, I’d do that as soon as you can. That way, you can make sure the feelings you have for your boss are genuine and not just enhanced by the idea that he’s forbidden fruit. If it turns out your feelings are genuine and they’re reciprocated, I’d think the elation you’d feel to finally pursue the person you want would trump any feelings of “weirdness” that you might have getting dinner with a guy who once rated your job performance.
I have been dwelling on an old relationship that ended over two years ago. After my ex-boyfriend and I broke up, I had a lot of trouble getting over him. The terms of our breakup were never really made clear and it really bothered me. He had a lot of personal problems that he didn’t want to deal with at the time, and that I naively ignored. I never really knew whether the breakup was because of me or — and this is what I assumed was the case — whether it was because of his problems. He wanted to remain friends but this didn’t happen because I wasn’t OK with just being friends. Now time has passed but I still miss him. He was a very large part of my life (my first real love) and we haven’t been in contact since early 2011. Am I crazy for wanting to see how he is? Is this me still clinging to false hopes or is it just me caring about someone who was very important to me at one point in my life? — False Hope?
I suspect you already know the answer to your last question. If I were you, I’d try to accept that someone who hadn’t reached out in almost a year and a half probably has no interest in rekindling anything, and you’re better off honoring the special time you shared by keeping it in the past and moving on.
*If you have a relationship/dating question I can help answer, send me your letters at firstname.lastname@example.org and be sure to follow me on Twitter.