DEAR HARRIETTE: I have a roommate who is incredibly nosy, and it’s driving me crazy. He’s always asking questions that are way too personal, and it’s starting to make me uncomfortable in my own home. I try to be polite and friendly, but he doesn’t seem to pick up on the fact that some things are just none of his business. For example, the other day he noticed some medication that I had left on the counter and asked me what it was for. I was caught off guard because I didn’t think I should have to explain my private medical issues to anyone, let alone my roommate. I tried to dodge the question, but he kept pressing, and I eventually changed the subject just to get him to stop.

This isn’t the first time something like this has happened. He’s asked about my finances, my relationships and even my family, often in a way that feels more like prying than genuine curiosity. I’m all for having a friendly relationship with a roommate, but I feel like there should be boundaries, and he’s consistently crossing them. How do I set boundaries with someone like this without turning it into a bigger issue than it needs to be? -- Crossing the Line

DEAR CROSSING THE LINE: As soon as you can move out, do. You shouldn’t have to live with someone who does not respect your privacy. That said, you live with him now. Invest in a lockbox where you can put all of your important papers, medications and other personal items so that he cannot reach them under any circumstances. Put a lock on your bedroom door if you can.

Talk to him directly, and tell him you need to set clear house rules. These include everything from household chores to personal business. Let him know that your personal life is off limits. Ask him to stop the inquisition because you will no longer entertain the discussion. Then, simply don’t respond when he goes into unwelcome territory. If you don’t engage, he will stop talking to you ... eventually.

DEAR HARRIETTE: My wife and I are gearing up for retirement. We’re very excited. We came to the United States 45 years ago and have been working tirelessly ever since. Retirement will feel different for us. I’m excited, of course, but still a bit nervous. We don’t have any grandchildren yet, so we’ll have to fill our time with hobbies. Do you have any tips for our new chapter? -- Anticipating Retirement

DEAR ANTICIPATING RETIREMENT: Before you retire, make a plan. What do you enjoy doing, individually and as a couple? What have you dreamed of doing but had no time to explore? Put these things on a bucket list. Do you want to stay living where you are now? Many retirees downsize and move to more temperate climates. Think through your options based on your budget, and make this next chapter a time of exploration together. It can be a lot of fun if you set that intention.

(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to askharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)

DEAR HARRIETTE: A childhood friend of mine has been in a relationship for more than five years now. He and his partner live together and share a car, and he covers some of her expenses, etc. They are fully enthralled. But honestly, I get the sense that he was never truly fulfilled by his choice. He always tells their story as if things just sort of happened, not so much that he chose things this way.

Recently, he sent me a message saying, “I always told myself if I were ever single again, I would be open to dating you.” I felt offended, so I responded: “And I presume I’ve just been rotting away on a shelf somewhere in hopes of ‘if you were ever single again’?” He seemed tickled and shocked by my response. We haven’t spoken since. Why would he imagine that I was lying in wait somewhere? Why does he think his interest is so highly coveted? Am I blowing this out of proportion? -- Making Assumptions

DEAR MAKING ASSUMPTIONS: Your friend’s tone was certainly off-putting and presumptive. It is understandable that you would have been turned off by what he said. But I have another question: Were you ever interested in him? Could he have detected any longing on your part that he was responding to? Even if that were true, it doesn’t make his couched revelation OK. That’s weak. So, beyond your knee-jerk rejection of his comment, take heed. You don’t need to get involved with someone who feels so highly of himself that he speaks through that tone to you. It’s OK to be offended, but don’t stew in it. Keep living your life.

DEAR HARRIETTE: I am an active member at my church. I attend regularly and know most of the congregation. I’m always helping out by giving as much as I can, whenever I can. One of my known ministries is offering rides to church members who do not have proper transportation. I drive for a living, so the church is happy to have me for field trips, house visits, etc.

If I’m being honest, I can be a bit of a yes-man when it comes to church affairs. Recently, an older woman at the church organized a group of people to visit a sick member who lives about an hour away. She contacted five to seven people, told them a date and time and they all agreed. She didn’t ask me about my availability; I don’t have a ton of spare time to make trips like this. When she finally asked me, I told her I couldn’t because I had plans already. She has been calling my wife, our pastor and other church members saying “shame on me” sort of things. I am always at everyone’s disposal, but I realize that maybe I’ve spoiled them. Should I address this with the church? -- The Driver

DEAR THE DRIVER: Yes. Speak to the pastor first, and share your concern about this woman’s reaction to your unavailability. Without being defensive, point out your long-term commitment to serve in many ways, including driving -- but your schedule must be considered. Explain that you feel hurt by this woman’s behavior and misunderstood as a result by the church. Ask the pastor to say something on your behalf.

(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to askharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)

DEAR HARRIETTE: I made the mistake of getting involved with a co-worker. At first it seemed really harmless to me because we were accustomed to hanging out socially (mostly in groups after work). When he asked me on a date, it felt like a natural progression. After a few dates, we progressed some more. Things started off as a fun and casual hookup, and then I began to notice that he seemed like he wanted our co-workers to know. We didn’t set those boundaries in advance, but it was an immediate turnoff for me. I told him we should keep things friendly and professional, as blurring the lines was getting uncomfortable for me. He conceded. But now he sometimes sends me inappropriate messages while we’re at work. How do I end this? -- Bad Choice

DEAR BAD CHOICE: Invite him out for coffee or drinks, and tell him that while you enjoyed hanging out with him, that part of your friendship is over. Add that you do not appreciate him sending you inappropriate messages at work. Invite him to stay professional. You both are building your careers. Encourage him not to allow a moment of fun to distract either of you from your goals. After that, ignore any of his advances.

DEAR HARRIETTE: Please allow me to help letter writer "Sibling Disconnect" in their predicament with their much-younger sibling. My eldest sister and I are more than 10 years apart in age. Still, my sister played an active role in my life, though more in the roles of parent, mentor and protector than that of a sister. She took me to art galleries, museums, water parks, zoos and on countless picnics. She took me to "fancy" salons to get my hair styled -- 50-plus years later I still remember being treated like a princess on that outing. She bought me pretty dresses and encouraged a love of reading and of music. She gave me her time. She listened to my interests and encouraged them.

I was quite young when she moved out of our house, and when things got bad at home, she “rescued” me by offering me a safe haven in which to live. When she married and moved far away, we maintained contact.

Fast forward many decades, and my sister is now effectively a shut-in -- she prefers books to people and is a certified bibliophile -- and she is content with her life. She is on a fixed income, and I now send her “care packages” whenever I am able: I send her groceries, treats and gifts she enjoys (usually books, but sometimes journals in which to write, or office supplies, stamps, etc.).

I do these things out of an abundance of love and gratitude for my most amazing sister, who all those years ago took time to get to know her little sister. It is my hope that she gets as much joy from them as I did from all the kindnesses she showed me. My sister is my hero. “Disconnected” has the opportunity to be the same to her sister, and I hope she embraces the role, because she has an incredible opportunity to be the person who makes the difference in her young sister's life and formation. -- Grateful Younger Sibling

DEAR GRATEFUL YOUNGER SIBLING: Thank you for this powerful testimony to sisterhood.

(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions toaskharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)