Morning Quickies: “Should I Tell My Friend/ Co-worker/ Former Hookup That I Hooked Up with His Roommate?”

About three months ago I realized I had feelings for my co-worker, Joe. He left our job but then came back years later. One night Joe asked me to come over to his house to hang out. We ended up Netflixing and chilling. It was great, but I worried about any awkwardness at work. So I decided to tell him that I have feelings for him and to ask him if he likes me. He said yes but that with everything he’s been through with his ex he’s trying to focus on himself. Then he led me on for the next month or so. We hooked up again. Then, out of the…

“My Boyfriend is Joining the Military And I Won’t See Him For Six Years”

My boyfriend, “Ted,” is joining the military this year. He told me in June, and we have spent the months since learning about the military and training him for it and talking about what our relationship is going to have to go through. He wants to join an elite group at some point, and he recently reiterated the fact that I will not see him very much at all for six years. My problem is that he keeps telling me I don’t have to do this with him, I can leave and that’s ok. He even said he’s fine if we “ride this out till I deploy and then break up.” I…

Morning Quickies: “Should I Get a Different Job Before I Propose?”

I have been dating my current girlfriend since 2006. Before then we had an on-again, off-again relationship for years. I have been struggling with when to ask her to marry me. She works as a veterinarian. In fact, that is how I met her — through taking my cat to the vet. I’m just nervous about whether we would have enough money to stay afloat. I work as a cartoonist for my town’s local newspaper and that pays decent. However, I do have some expenses such as my aforementioned cat along with a dog. On top of that there is food, television, and other such things. Should I try to find some…

“He Ghosted Me After We Hooked Up, Then Texted Me Five Months Later. Should I Respond?”

Your website has helped me a great deal in the past (he wouldn’t even pay for my McDonald’s birthday lunch) and I come to you again with another peculiar love situation. Please feel free to share it wherever possible in the hopes that others in a similar situation may relate and find the means to get through a tricky situation. In about June or July last year, I met a guy through an sex buddy website. We met twice and he stood me up the third time stating he was tired. He messaged me a few days later to apologize, but I responded in an unbothered way. I deleted his number but…

“My Friend Thinks I’m a Charity Case”

My childhood friend and I recently reconnected after more than 50 years! We got together for an overnight visit while I was in town for the holidays. I loved seeing her, and now we exchange calls, texts, and emails a few times a month. She works at a great job and is living well. Her apartment is so nice and she looks fabulous! I suffer from chronic depression and have had to face a lot of challenges without support from a loving family or a support system. I manage my life as best I can, living within my means but not in a state of misery. While I was visiting my friend,…

“It’s Been Thirty Years and He Still Won’t Travel With Me, Give Me Birthday Gifts, or Even Bathe”

My significant other, “Chuck,” and I have been seeing each other for 30 years — yes, 30 years. It’s a long story but I will not go into that. He used to give me birthday cards and gifts and Christmas cards and gifts, but in the past nine years he has become uninterested in doing those things anymore. I have always gotten him a card or a gift or have done something special for him on his birthday. He doesn’t reciprocate anymore and I am getting fed up with it. I went to Chuck’s house to make him a lovely prime rib dinner for Christmas after I had already purchased him a…

Morning Quickies: “My On-Again Boyfriend Hangs Out With His Ex-Girlfriend’s Grown Daughter”

Okay, this is very complicated to me. My daughter’s dad, “Carlos,” and I were together for nine years before we split in 2017. He left and started a relationship with a person we both knew, “Ginger.” He says he didn’t plan it that way, but okay. Well, while he was with Ginger, I also started a relationship with someone we both knew. I didn’t plan it like that either — we were supposed to meet and have sex and go our separate ways. But okay. It developed into a relationship. “My Boyfriend Has Remained Close to His Ex’s Daughter” Well, Carlos and I got back together at the end of 2018 and…

“My Boyfriend is Raising His Ex-Girlfriend’s Kids and He Won’t Get Rid of Them”

I just reunited with my first love after 30 years. He has never married but has two kids from a previous relationship whom he’s raising. That’s all wonderful, but here is the kicker: When he got into a relationship with the woman, she already had three kids who were from multiple men! They became “blended” and then had their two kids together. Well, that didn’t last long before she bailed and left them for a life of drugs and men. He stayed with all the kids. Now, fast forward to today: The oldest is 19 years old and has moved out, but that leaves four kids living with my boyfriend, aged 17,…

“My Boyfriend Doesn’t Want to ‘Set Off His Dad” By Moving”

My boyfriend, “Bruce,” and I have been together for three years now and living together for about a year. We live in a town that is about 45 minutes away from both our jobs. I want to move out so we can be closer to where we work, but Bruce doesn’t want to because we rent from his dad and he doesn’t want to set him off. We have no lease with his dad, and we’ve been paying rent in a home that is unfinished (as in, a good 1/3 of the house doesn’t have any flooring installed, no baseboards are down, etc). There are cheaper options closer to our jobs and…

“My Friend Wants to Stay in My Vacation Home for Free. Do I Have to Let Her?”

I’m having a problem with a “friend,” “Janet,” who is married to my husband’s best friend. I don’t have a problem with him, but Janet has been very pushy over the years. We have gone on a few vacations together. Every time she has done something extremely annoying, from complaining that her room wasn’t ready early enough and demanding free breakfast from the hotel to complaining that no restaurant menu has anything she can eat to overstaying her welcome when she was invited to our vacation home for a few days. She claimed she couldn’t book the same flights we did and had to stay in our vacation home longer than we…

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