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By Jessica Lanyadoo

Hi Jessica,
My boyfriend is in his early 20s and a bit younger than me, but doesn’t have a career path. He’s smart, capable, and has a diverse range of talents — I believe he could do anything if he applies himself. However, when he tries something out and it doesn’t manifest, he gets discouraged easily and questions his abilities. I’m established in my career and recently received a promotion. I’m also always busying myself with some side business or another in anticipation of having my own business one day. I rarely question my ability and know…

Hi Jessica,
My boyfriend and I have been dating for about four years. I’m really in love with him, but lately I feel really bored too. I feel so guilty, but I just can’t shake it. He still tries to be romantic, takes me out on dates, buys me flowers, etc. Our sex is fine, as fine as it’s ever been. When I think about seeing him in the evenings after work, though, I just feel like, ugh. Boring. Same old. It’s horrible, and I’m afraid if I don’t fix this feeling, I’m going to sabotage the greatest relationship I’ve…

Hi Jessica,
For the past year I was involved with an emotionally unavailable man. We were never an official couple although I wanted more, and I settled for the pittance of attention and, frankly, phenomenal sex just to get by.
I would develop feelings for him and then call it quits. After a month or so he would do something very romantic and thoughtful to pull me back in. He’s a charming, good-looking man who I know sleeps with other women. I was sleeping with other people too throughout the duration of our time together but emotionally I had fallen…

Hi Jessica,
I have a wonderful boyfriend — very affectionate, cooks me dinner most nights, tells me how much he loves me, deals with my dysfunctional family with grace, and in every way but one is off the charts. The problem is that he doesn’t seem to care about having sex. And I care very much about having lots of sex. After being together for five years, we only have sex a couple times a month, and I am always the one initiating it. When I try to talk to him about doing it more often, he gets very defensive…
By Jessica Lanyadoo

I tried, and failed. Multiple times. Nothing I try — everything I want and believed I could do and achieve is impossible. Now what? How does one learn to accept a lonely, meaningless, and pointless existence? — R.A.J.
I wish I could ask you some questions, RAJ. Like how old you are, what you tried, and how you know it’s impossible to get past where you struck out. I don’t want to be a Pollyanna and tell you that everything is great and you’ll be great, because the truth is that in life most of us don’t…

Getting an immigration visa is like playing Cones of Dunshire, the fictional game from Parks and Recreation whose rules are so convoluted that even Ben Wyatt, its creator, can’t explain them. As anyone who’s endured the process will tell you, it’s an emotional roller coaster and an administrative nightmare marked by endless paperwork and instructions that are devoid of any actual instruction.
I spent my first five years in the US holding onto the thread of various H-1B work visas that led to some utterly redonk bureaucratic scuffles, including an HR “snafu” (their word) that forced me back to Blighty…

I recently started dating an amazing guy that I’m very into (yay!). We have fun together, the chemistry is awesome, and I’m very excited about where our relationship is going. However, shortly after we got together, we realized that he had given me an STI. He was asymptomatic, and it’s an STI that is hard to test for in men (we were both tested before we started having sex). Soon after we had sex, I started having symptoms, and it’s been a huge pain (the symptoms suck, multiple treatments aren’t working, the doctors visits are intrusive and expensive, etc.).
While…

Hi Jessica,
I reconnected with a younger person on a shared project. She came on pretty strong romantically, then sexually. We had fun times for about four weeks, but then she announced that she “couldn’t do this.” I was stunned by the sudden reversal but did not blame or shame her. I just told her, “You feel what you feel, s’okay,” and assured her that we will remain friends. Why do people start out so hot and heavy, only to neck-snappingly change? (Hint: she is 19 years my junior.) I do want to trust younger partners, but day-um. — DS
…

Dear Jessica,
My partner and I recently celebrated our 6th year together. But, to be honest, I responded to this occasion with mixed feelings. While he is my best friend and has brought so much joy into my life, the reality is that he has been financially unstable and indecisive about his career and life direction over the past couple of years. All of this (particularly the financial piece) has ultimately had a big impact on how I feel towards him. I feel that supporting him has really held me back. Not to mention his lack of clarity creates tension…

Hi Jessica,
My boyfriend is one of the most thoughtful people, and he makes me blissfully happy. We have the same fundamental ideas about life with enough room for differing opinions to keep things interesting. But there is one thing we disagree about that is driving me nuts.
It seems like every time there is an issue in the news that relates to women’s rights — whether it’s legislation preventing rape on college campuses, companies that fail to pay women equally, or, most recently, the D.C. judge that overturned the case against the man who was taking creeper photos up…
Celebrating the free-wheeling spirit of the Bay Area — one sentence at a time.