Dear Dr. Wes & Jenny: Ever since my daughter was 13, she has liked older guys. When she was in seventh grade, she was “dating” ninth-graders. At 16, she hasn’t dated any high school guys. They’ve all been 19 to 22. Worse, when I was complaining about this, she tried to tell me that there are girls her age having relationships with guys in their 30s. When I asked why I don’t hear about any of this, she says they keep it a secret. I divorced when she was young, and her dad has almost no relationship with her. I think that has caused part of the problem. I am getting really worried about all this. What do you think?

Wes: I think you might have a problem. If she were under 16, there could be legal concerns for anyone sexually involved with her. However, given her age, that’s a topic for a different day.

I’ve actually had several such cases, and the outcomes vary depending upon the quality of the older partner, who is typically – but not always – the guy. I actually have come up with a “rule” for these situations that your daughter might want to adopt: The older the boyfriend, the more perfect he has to be. If one is 16 and dating a 15- to 17-year-old jerk, it doesn’t matter as much in the long run. As a wise teen girl once told me, “This guy will be gone in a few weeks : me and my parents will be dealing with these issues for years to come.” A 16-year-old dating someone 18 or 19 might not be the worst thing on earth, if the guy is pretty high quality. It always upsets high school boys (I hear them groaning already), but some teen girls really don’t fit in very well with their peers. Some just feel more comfortable dating a guy in college or in his first job out of high school. If the older partner really is mature and a good influence, I’ve actually seen it work out very well.

The key question is why an older guy is dating a younger girl (or vice versa). If the answer is that the younger person is unusually sophisticated and mature, I think you may have a good love match. However, a 19-year-old who hasn’t gotten over being 16 yet and is therefore dating kids his/her own emotional age is almost always bad news because they have most of the rights of adulthood and none of the maturity. If your daughter’s guy fits into this category, then you have cause for alarm.

Obviously, this only gets worse when your teen is dating someone in his 20s. There MAY be times when a 16-year-old matches well with a 20- or 21-year-old, but I haven’t seen many of them. It’s just hard to imagine a teen so fascinating and sophisticated that a 21-year-old would forgo all the trappings of an age mate to date them. The larger the span of years from that point on, the more you find a developmental mismatch that no amount of perfection can overcome.

Of late, I am also hearing stories of 16- and 17-year-olds dating thirtysomethings, and frankly I’m baffled. If your daughter starts heading in that direction, I urge you to head to the therapist. However, don’t expect an instant cure. When I have dealt with these cases, we quickly find that the Romeo and Juliet syndrome kicks in. The more we explain the foolishness of the situation, the more attracted the younger partner becomes. So in this case, the therapy can never be about breaking up. It has to be about challenging the young person’s thinking. As Jenny notes below, that can be a very tricky proposition.

Jenny: I have seen these relationships work out, and I also have seen them fail miserably. I agree with Wes: It all depends on the reasons the older guy is dating a younger girl. Having been through high school in a town where there are two colleges close by, I have to say that it isn’t hard to find guys who have grown up and gotten over their immature phase. Most of these older guys, I think, stop caring only about who they will sleep with next and may actually be the kind of guys you want your daughter to be dating. In the end, the relationship really depends on how great the guy is and how emotionally compatible they are.

I can see a 16-year-old dating a freshman in college, but once the guy reaches 20 or 21, there needs to be some caution taken. Guys this old have seen life and experienced a lot that your daughter has not. It’s easy when you are dating someone older to forget about the age difference, so a quick reminder could help her understand your opposition. There are older guys who just look for the next score, and hopefully your daughter isn’t going after one of them. If she is, it will only lead to heartbreak.

By dating an older guy, she is trying to establish herself as more mature. Telling her she can’t date someone older will only push her to rebel. It is the classic “I am older and more mature, yet I will still act like a teenager when opposed” syndrome. So your level of interference should be that of a watchful eye because it is her turn to learn. You can still enforce the rules, and if you really are afraid she might be out doing something she isn’t supposed to do, have her call you every hour or so to tell you where she is.

And have her bring over the guy she wants to date. You may think he’s going to be a sleazeball, but once you meet and spend some time with him you might change your mind. This also will test his dedication to your daughter because, lets face it, not many guys want to meet the parents. However, if he respects your daughter, he will meet you and try to make the best impression. If you aren’t satisfied when you meet the guy, then you need to sit your daughter down and voice your concerns and then hear her out. That is the only way to avoid a huge conflict down the road.

Next Week: New technology allows parents to surveil their teenagers’ every move. But should they? The ethics of teen tech.