Dating

I’m Over 30 and Never Been in a Relationship. How Do I Not Be Single

Hey Tot—
I’m single and just turned 33, and have been single for 33 years lol. Plus, sex isn’t really a habit in my life including self-pleasure. I don’t know where to begin when it comes to dating, a relationship, or building a healthy sex life.
I am an actor currently touring the country with a Broadway musical. I am verse/bottom. I am pretty handsome. I am also inexperienced, and it weakens me a bit.

Where do I start?

-ART

Dating, relationships

I Pay the Mortgage, But My Boyfriend Won’t Add Me to the Deed

Hey buddy…I’ve read your stories for a while and never thought I’d need your advice but here I am…lol…so me and my dude have been dating for two years…we’ve been permanently living together for about a year and a half…he bought another house so we could live together…i pay the mortgage and the condo fees and he pays the utilities…we’ve been disagreeing because i want more stability if something happens to him… like my name on the deed of the house…but he’s adamant against that.

I took out an insurance policy on myself for him if i were to die…he was supposed to get one on himself for me but couldn’t because he already had one with that company and doesn’t want to do the medical portion of it…not sure why, but it is what it is…his solution is if something happens to him I get to live in the place until I decide to move…that’s not fair to me…i feel like i should still have just as much stability as he will if something happens to me…how can i explain myself more to him or am i being unreasonable…all of the people who I’ve spoke to about it, the people i confide in, have said that I’m not being unreasonable and that if he doesn’t see my point then maybe i should reconsider living with him and paying his mortgage…I’m torn…i love him but I’m also at an age where i can’t take those chances…i feel like if we’re going to be in a partnership then we need to be partners…not him in charge and me playing house…what do you think?

 

-Black

Dating, relationships

Five Years into a Relationship and He Cheated Year Two

 Hi,

I have been dating my long-distance boyfriend for almost 5 years now. We live in different countries, but every time we can, we travel to one another. This past summer, we even got married, and our whole families were happy about it. Everything seemed perfect! Today, he opened up to me that , 2 years into our relationship, he cheated.

He kept it from me due to the fear of losing me. I am so hurt by what he did, because I thought we were strong enough to surpass those physical temptations. He says that he couldn’t live with himself anymore knowing that he’s hiding this from me, as every day he’s realizing more that I’m his soulmate. Before this happened, we were planning on him moving to the states so we could spend our lives together. I see that he’s remorseful because he could’ve still kept it a secret, and I would’ve never found out. However, I hate to admit it, but my ego is bruised, and my heart is shattered. I would like to think that we can make this work, but I’m afraid that I’m not strong enough to. I’ve always said that I would immediately break up with someone that cheated on me , but it is so difficult because I’m in love with him. Am I weak to try this again? Or should I even? That betrayal has scarred us forever.

From,

J

Dating, relationships

We’re in a Relationship Now, But He Cheated When We Were Dating

Hi T,

Seeking advice and hoping you can help me out. A few days ago I found out my boyfriend of 4 months actually cheated on me when we first started dating. Hopefully long story short, I ran into a friend of a friend at a bar and we were talking. I told him about my boyfriend and how long we’ve been dating, and that’s when this friend of a friend hit me with the “oh that’s interesting” BS. I asked him what he meant by that, and that’s when he said he knew someone who had hooked up with my boyfriend which would have been about 5 months ago. The problem is, my boyfriend and I were dating 5 months ago.

I tried to save face in front of this guy, but when I left I was pissed. My boyfriend and I got in an argument, because I hate feeling blindsided, and I feel he cheated on me. I get we weren’t official until 4 months ago, but at 5 months, I thought we were just dating each other. While we haven’t’ broken up, things between my boyfriend and I are a little rocky. Just don’t know what to do in the situation. Could use the advice.
-Benny B

Dating, relationships

He’s Committed to Me, But Wants to Sleep with Other People

T,
I have been with this guy for 2 years and we broke up. I was head over heels, I would have done anything for him. He didn’t have to say it but I knew he wouldn’t do the same or couldn’t. He had some demons he needed to take care of.

Well, we were broken up for about a month and we got back together. It’s been a few weeks and things are tremendously better. Everything has been so passionate and intimate, he shows so much affection, he never did before. He told me he wants to spend the rest of his life with me and he’s never said that to anyone ever.

The problem is, he wants me and him to hook up with other people together. He wants to have more experiences (he’s already had past experiences with ex-girlfriends). I expressed to him I’m not comfortable with it. Just thinking about him sleeping with other people hurts, watching him sleep with somebody else would just rip my heart out.

He doesn’t want to break up, at least not right now is what he says. Both of our personal lives have been going downhill and it’s like we lift each other up. But I know me not wanting him to sleep with other people is a deal-breaker. He wants to see if one of us will come around eventually but I think if we stay together the heartbreak will hurt even worse. Being with him has been so magical, I feel amazing, but I can’t keep this on the back burner until we start having problems or he gets bored with our sex life. Any advice?

-Madison

Dating, relationships

I’m Ready. Should I Have the Relationship Conversation?

Hello Tavion,

I’ve been a big fan of you for a while now and can’t help but appreciate all that you’re doing.

I need your help!! I’ve been dating very active lately and I’ve been lucky to meet some pretty cool people. Some, I have gone on multiple dates and hang out with a couple of times.

Through this process, I met a guy who seems to be the one that I can finally commit to and build a relationship with. He is exactly what I’ve been looking for in a significant other. Getting to know each other within the last one month has been amazing.

I actually think I am kinda falling for him. But the gag is, he is moving back home.

He has been here on a student visa and now that he has graduated it’s been hard for him to find a job forcing him to move back home. We’ve literally been in a relationship but without the title. He is friends have become my friends and vice versa. He is older by 6 years and has experienced everything you can imagine in his past relationships (The good, bad and the ugly, long distance, toxic and abusive…. etc).  His last relationship ended in January and since then, he has been on a journey of self-care finding himself and falling back in love with himself.  I guess my question is how do I go about having the conversation about this? I definitely want something more (EXCLUSIVITY and all) but I don’t want to be the rebound guy as well or rush him into something he might not be ready for.

Should I just let the chips fall where they may? Should I be completely up-front about my feelings?

Thanks,

Victor

Dating, friendship

Should I Tell My Friend to Break Up with Her Boyfriend

Hey, if you don’t mind keeping this anonymous.

So today my best friend was getting hit with a rubber band which ofc was leaving markings and everything. She was getting hit with the rubber band by a kid that she talks to but they aren’t really “friends.” Let’s call him “Jose.” Okay anyways she was telling Jose to stop hitting her and he wouldn’t, then this kid that has a crush on my friend said to stop and tried to make him stop but Jose still didn’t. (Note I wasn’t in her class) but so here’s the problem, my friend’s boyfriend was sitting in the table behind her while this was all happening and not doing a thing about it but he knew it was happening. Also that for the past two weeks they haven’t had an actual conversation. Besides all of this, my friend wants to know what I would say to him if I were going to. I just don’t know how to write it.

-R

Dating

In Love with a Roommate Who Wants Someone Else

Hi T,

Here’s the situation. I was dealing with a guy that I had strong feelings for. He didn’t have as deep of a connection for me as I did him. We talked and we became friends, very good platonic friends. A few months later we become roommates. I moved into his home renting a room. Things are great, I’ve had my overnight company, a friend visiting from out of town.

Recently, he’s started having a local consistent friend stay overnight. For whatever reason, I’ve become bothered by this. I don’t know why. We were never together. In hindsight, I can acknowledge that. I openly accept that he and I aren’t supposed to be together. He has had people come over, they did whatever they did, and they’d leave. I don’t know why I’m feeling bothered by my friend finding someone he can spend time with consistently. Can you help me process this?

Confused AF

relationships

I Found Out My Aunt Has Been Dating My Ex for Two Years

Hi, I really need some advice. I just figured out my aunt has been dating my ex-boyfriend for about 2 years. I don’t think either of them knows that I’m her niece. This guy I was almost engaged to and I had helped him pick a house out that now my aunt is going to live in. It’s been 10 years and we only broke up because my uncle who I lived with at the time told my ex whopper lies. I’m so hurt and I just don’t know what to do? How do I tell my aunt without wanting to punch her and scream at her?

-Brandy