My boyfriend calls, texts or e-mails me daily but only wants to go out about once a week and never agrees to a day or time until the last minute. We met at a singles event and he really chatted me up. He also kept me laughing with stories of his dating adventures. He’s 40-something, has never been married and has had only a few relationships. One of those relationships was two years long; the others were less than a year. Is this a red flag? I love him and the sex is fantastic but I also feel uncomfortable around him, like I’m not quite what he’s looking for. Sometimes I want to end it and other times I think he’s changing and everything will get better. I just need to know: Is this relationship going anywhere?

You can quickly check if a relationship is advancing from casual dating to something significant by asking yourself four questions. Does he want to see you more than once a week? Does he introduce you to his family and friends? Does he make solid plans for a vacation with you? Does he talk about his future plans and include you in that vision? If not, he’s probably a casual dater. Especially if his relationships tend to be short and he’s well educated in how to meet women and initiate dating but has failed to develop the ability to keep a relationship going. The other possibility, of course, is that he’s just not that into you—but hasn’t met anyone else yet. And although this may not be the case with your man, sometimes people who fail to make plans are also romantically involved with someone else.

I think that you must already be pretty attached to put up with this last-minute lothario. You deserve better. Treat yourself like a woman of worth by not waiting for his “yes” before you make plans. If you ask him out for Friday and he pulls the “I’ll let you know,” give him a deadline: “OK, but I need to know by tomorrow at 4 p.m.” If he doesn’t call by 4 p.m., he’s signaling his ambivalence toward you and the relationship. Don’t be blue, just make plans with someone else. Use this relationship to learn how to take sweet care of yourself the way anyone who genuinely loves you would.

My son and his girlfriend text message each other 50 times per day—no kidding—even though they see each other about twice a week. The bill is killing me, but he’s a good kid and reliable, with excellent grades and a starting position on the football team. My wife suggested that I write to you because she thinks the contact is excessive for high-school kids. Other than the money, I don’t have a problem with it. What do you think?

If your son is in high school, he can get a job and pay for his own cell-phone bills. If he can’t make or save enough to fund a monthly plan, he can purchase a pay-as-you-go phone. Or you can pay for basic service on a basic cell phone so you can contact him in emergencies, but he’ll be responsible for any additional minutes or services. Failure to pay the bill results in less freedom, like a shorter curfew or less time with his girlfriend. After all, if you don’t teach him money and time management now, you’re bankrupting his financial knowledge base, which impacts his future more than his high-school grades. The second issue, obsessive texting, can be found in every relationship based on infatuation but not in any relationship based on true friendship or genuine love.