This week we have questions ranging from the courtroom (divorce… nothing that scandalous!) to the bedroom….

Question: A match says he's separated but divorce not final yet (almost). Avoid? Alarm bells ringing.

Answer: I don't like absolutes. Especially if someone has children, certain states/countries require you to be legally separated for a period of time before the divorce is allowed to be finalized.

If alarm bells are ringing for other reasons, you can certainly listen to them, but with this information alone, I wouldn't immediately make it a "no." I would instead simply date this person and see how it feels. Plenty of people have left a relationship long before the divorce is final. And sure, some people are not ready to date yet. But I couldn't make that discernment here. I do appreciate your date's honesty. There is something to be said for that.

I have said this before and I will say it again, with no connotation but simply based on patterns I have seen: Women are much more judgmental of a separated man than men are judgmental of a separated woman.

Question: Good dates but no attraction. How to feel less guilty rejecting people?

Answer: I have two answers to this one, and I'm going to go in backward order:

1. You should never feel guilty rejecting someone as long as you are kind and tactful, using a script like the one below. Do not ghost.

“Thanks again for such a fun time the other night! Unfortunately, I’m just not feeling the connection I’m looking for, but I wish you all the best!”

2. How are you evaluating attraction? I ask because I have to wonder if you are looking for too much attraction on the first date and discounting a nice connection. Attraction can often grow if you give it a chance. Sometimes not, of course. And if you're 100% certain it could never be there, there is no sense in going out again. But if there is a question mark (especially since you said they are good dates), it never hurts to go on another date. You're not promising anything other than to give things a chance!

Question: Four great dates, now he’s away for work for 10 days. Doomed?

Answer: No need to be so catastrophic!

No, you are not doomed. Not everything has to be the end of the world.

Ask him this right now: "How much would you like to be in touch when you're away for work? I don't want to assume anything!"

This is great practice in managing your own expectations and speaking up. Then, depending on the response you can say this: "Do you want to get the next date on the calendar for when you're back?"

Question: There's a bit of a problem in the bedroom. How do I bring up medication?

Answer: This is tough because I wish he was the one to bring it up or simply take action on his own. The time to bring this up is not in the bedroom.

"I have something a little awkward to bring up. I want to make sure we're both having the most fulfilling sex life we can have. And I'm bringing this up because I plan to keep having sex with you! I know sometimes things don't go the way we want in the bedroom. Have you ever considered talking to a doctor about it?"

This is a difficult conversation to have, for both of you. I like starting with the line about it being awkward because it breaks the ice a little bit. As we know, men are very touchy about their parts. His reaction will tell you a lot. Does he prioritize his ego or take what you have to say seriously? And sadly, erectile dysfunction is much more common than people think because nobody talks about it. Sometimes it's as simple as switching antidepressants or something like that that may be interacting with it. But I have no idea.

©2026 Tribune Content Agency, LLC