But I’m willing to give it a try. Please, ask me. :-)

The very first thing you should consider is the fact that dating a friend’s sibling can, and often does, get very messy very quickly. The odds of your friendship quickly crumbling based on how well or how poorly your dating relationship with their sibling goes is fairly high. If this is a friend you’re willing to chance that with, then just know that I warned you about it first.

That said, your intuition is not a good basis for deciding if someone is or is not interested in the same sex for the purposes of dating, and using previous individuals one has dated in the past is not a good measuring stick for what a person is apt to do in the future. Sexuality is, after all, fluid, and women, more so than men, have a tendency to move up and down that line quite a bit in their lifetime.

I always encourage people to respect other’s boundaries, but, if you want to put your mind at ease and move forward one way or another, you should gather your personal reserves of courage, ask the sister out for coffee some place neutral, and simply ask her. You need to talk. Don’t put her on the defensive, and do not, under any circumstances, be demanding. Instead, be open and honest with her. Tell her that you recognize she’s set these personal boundaries and limits, you understand she’s said in the past that she is no longer interested in dating the same sex, but, if she should reconsider, you would very much like the chance to take her out on a date.

Be forewarned, this conversation could backfire on you. But, frankly, the direct approach, though sometimes immediately messy, is often the best way to prevent long-term messiness from happening.

You don’t know until you ask. One way or another, you’ll have your answer and can move on from there, if that’s what you really want. It’s all very risky regardless of what you do if you choose to actually pursue her in anyway. Please be aware that you risk a friendship anyway you go.

Please, ask me a question!

I think it sounds as though she isn’t pulling her weight. A relationship is a partnership. That means that each of you should be pulling 50% of everything, including chores. If she’s not really doing that, then you have a valid complaint.

Instead of telling her how you feel, it’s time to sit down and write out a chores list. Yes, I realize this sounds like something you would do with a child, but, if she’s going to act like a petulant teenager, then she needs to be treated as such.

Tomorrow, tell her it’s time to redistribute the chores, pull out a pen and paper, and write out everything that needs to be done at home both daily and weekly. Then, between the two of you, separate out the chores between what you will do, she will do, and what you’ll do together.

Once the schedule is worked out, stick with it. Don’t do it if it doesn’t get done. Leave it. It will be the hardest thing you’ve done, but leave it anyway. After things begin to pile, you’ll have plenty of evidence to prove two points.

First, it will show that she’s not pulling her weight after agreeing to do the chores. Second, it will show everything you’ve been doing this whole time to prove you’re not overreacting.

And I’m ready for your questions. Please, ask me.

The very short answer is nothing.

Not knowing the specifics of why your friend is speaking with this other person, it’s hard for me to give you advice on what to do, but I can give general advice on people and how they behave.

I find you humans to often be irrational when it comes to your emotions, and you’re apt to see only what you want to see if you have the slightest hope that something you want may happen. If your friend has hope, even just a micron, for a particular outcome happening with this other person, that could explain why she’s hanging on.

Other people need the drama. They may not want to admit it or recognize it, but they enjoy constantly being in a state of being miserable. It keeps them going; they are self destructive, and no one can keep them from that path but themselves. Most would call these people “drama queens”. Perhaps your friend is one?

Another possibility is that your friend is lonely, and this other person provides some kind of companionship even though it is negative. To some, negative is better than none at all. Many abused spouses/significant others remain with their abuser for fear of never being able to find someone else. Perhaps your friend is afraid she wouldn’t find many others to share her life with?

Whatever the case may be, it is evident that your friend isn’t truly looking for your help. If she was, she would take your advice. She’s looking for an ear and a shoulder, which is the only thing you can actually provide at this point. When she asks you what to do, tell her you’ve given your advice already and that you can give no other. Then ask her if she’s taken it. When she tells you no, tell her there’s nothing more you can tell her. It may end the conversation, but that is doubtful. Instead, she’ll provide arguments or commentary on why she’s still in this relationship. All you can do is listen. If you’re tired of listening, perhaps its time to tell her you’ll be there for her when she decides to move on, but, at this time, you have to move on from her.

is, “Yes, I know you have a pregnant wife and a child. You mention it EVERY CHANCE YOU GET”, but I’m getting really fed up with having to listen to it every time I encounter her. Is there any way to talk to her as the adult and, no doubt, interesting individual she is without having to always have the conversation degrade into talk of her family (assuming it didn’t start there to begin with)?

Some people become fixated. When their life revolves around something, they forget that other’s lives do not. That can be quite challenging for everyone else if they are into the same interests.

On top of that, family is always a hot button issue, and many people feel that you’re being questionable or negative if you say anything but good, warm, fuzzy things about their family, so telling this person that you’re tired of hearing about their family, even if you do so politely, will more than likely end in something you’d rather avoid.

What to do?

You can start by trying to steer the conversation away from the topics that you’ve grown wary of hearing. When she mentions her child or pregnant wife, you mention something else and politely change the subject. It’s the best you can really do. If she doesn’t take the hint after a little while of you gently trying move the subject matter away from her family, she will never take the hint, and you’ll have to decide of getting to know her better is worth the hassle of dealing with the world revolving around her children and wife.

That is a hard one. Long distance relationships can be difficult. Though not impossible, at some point one or both of you will have to decide to give a little or a lot and move. Right now, whatever is working for you is what’s best to do, but, if this long distance relationship becomes the ultimate long term relationship, you’ll have to figure out which one of you is willing to make that sacrifice and move.

My advice to you is to ask yourself now if either of you is willing to budge should this become the forever-and-always type of relationship.

Apparently, having enough time to build that birdhouse was a bad sign. If you have questions, please send them my way.

Why label at all? People who ask you “What are you?” are rude, nosy, and need to mind their own business. The only reply you need give them is, “Human and in a very happy relationship, thank you.”