I’ve Lost Weight and My Boyfriend Gained Insecurity

Hi T,

I’ve been reading through your site and thought you had some good advice so I’m going to try this out. I’m having a problem with my boyfriend that’s really getting on my nerve lately. To give you a little background, over the past six months I’ve lost about 48 lbs and look the best I have in a minute. My boyfriend was initially very support of the weight loss, but over the last few weeks he’s gotten super clingy and possessive. I just don’t know where any of this is coming from. Appreciate the insight.

-New Me, But Not Who Dis

P.S., we’ve been together for over a year.


I Love My Boyfriend, But I Can’t Get Any Sleep at Night


I have a question for you. It may seem stupid compared to some of the questions you answer, but I’d appreciate your honesty. I’ve been with my boyfriend for a few months now, and everything is cool except this one thing. When I spend the night at his place or he spends the night at mine, I can’t ever get any sleep. EVER! He always tries cuddling up with me and sleeping right on top of me. I just can’t sleep with a person on me all night. For the past few weeks, I’ve been coming up with excuses as to why he shouldn’t sleep over or why I can’t sleep at his spot. I know I probably should say something to him about the discomfort, but when I’ve mentioned the issue in the past with my ex, my ex and I got into a dumb argument. I don’t want that to happen. So yeah, your thoughts.

-No More Sleepless Nights


I Thought We Were Vibing, Then I Found out About His Girlfriend

 Hey T.,

I have to admit that you give the best advice – I’ve been reading your page for a week and I’m already in love.

Two weeks ago, I went to a coffee shop with two of my friends and while we were having fun, I noticed that the waiter was interested in me. I kept playing with him as I had just broken up with my boyfriend and when I went to the bathroom with my friends, he came in and told me that he liked me but he was 10 years older than me. The next week I went back there and we exchanged numbers. Two days after that we went on a date and we ended up kissing. We talked a little over the next few days on the phone and I went back there after 5 days and he was totally flirting me and we made out again. He wanted to go out with me again but he cancelled our date because of his job. This afternoon I found some pictures of him and a girl on Facebook and I asked him if he was in a relationship and he replied yes, that our “thing” didn’t mean to be something special and that he’d rather I didn’t tell his gf about us. What should I do?


Dating, relationships

Infidelity in an Online Relationship

So I’ve been in this online relationship for about 7 months with this girl from California–mind you I’m from Illinois. And so she’s in college and I’m still in high school and we were planning on meeting in May which is kind of wild. And recently she got a little too drunk one night and cheated on me. We cleared everything up and now she’s doubting our future saying she doesn’t know if she can stay faithful again. And I’m just wondering if i should stay with because she doesn’t believe we’ll make it anymore



Should Exes Give Back the Gifts

Hey T,

Me and my Sister were watching some show, and in it, two people had recently broke up and the ex-boyfriend was demanding that the ex-girlfriend return all the expensive gifts he bought. But the ex-girlfriend wouldn’t budge, and kept telling him no. Which got me to thinking. When a couple breaks up, do you think people should return gifts?

Curious for the Future


Should I Stay or Should I Go?

Hey I’ve been in a 2 year relationship with someone I truly love but I don’t feel the love coming from him. He feels if he buys me things that everything will be okay. I’ve tried for 6-8 months straight to get him to understand where I’m coming from so we can have an understanding. He’s told me numerous hurtful things & we have cheated on one another. I’m trying to decide my place so I can know if I should move on or try to make it work.  Please help before I do the wrong thing.



I Can’t Quit My Ex

Dear T,

No matter how hard I try, I can’t shake my ex.  He and I have broken up four times, and each time we get back together.  This last time though, I swore I was not going to take him back.  I told him, and myself, I was tired of the petty arguments and sick of feeling like I can’t trust him.  The last time we broke up, it was because he cheated.  And I know all the reasons why I shouldn’t get back with him, but damn it I love him.  The good times between us are really good.  Great convo, great laughs, and great sex.  With him in my ear asking me for another chance, I’m tempted to take him back.  What do I do here?  I could really use some good advice.

-Hopelessly Stuck


Rethinking a Friendship

Dear T,

I have this colleague that I’ve worked with for about a year now.  Well for the past 8 months or so, we’ve started hanging out outside of work as friends.  It was cool hanging out with her at first, but now I’m starting to notice some things I don’t really like.  For example, when she drinks too much she has a bad habit of removing the filter from her mouth.  No lie, at a club one time she told this fine man “I bet you have really good meat, and I’m a little hungry.”  What made the line worse, is that the guy’s girlfriend was standing right next to him.  Coworker almost got me involved in a club fight.  And this is just one incident.  This girl also says things to my real friends sometimes that have them looking at her crazy, and me crazy for bringing her around.  I think I should pull back on my friendship with her, but not sure how to go about it. That’s where you come in.  Please help.


The Real Olivia Pope

Dating, friendship

Playing with Fire…..Dating a Friend’s Ex

Dear T,

Please don’t judge me, but I think I have a thing for my best friend’s ex.  My best friend and this guy broke up nearly 3 years ago, and I hadn’t seen the ex until about 2 months ago.  That’s when the guy started working in my office. Since then, we naturally started talking and have even become cool. And my best friend knows this. What he doesn’t know, is that his ex has started flirting with me heavy. And if I’m honest, I like it because I like him.  But, my mind keeps telling me that I can’t go there for the sake of my friendship. However, I’m tired of denying my feelings for this guy. Plus, my friend has moved on and has a good man. What do you think I should do?


Playing with Fire