Dear Eric: I’ve been dating my boyfriend for about five years. I recently reconnected with a friend from college who I’ve really missed. After we hung out a few times, I introduced my college friend to my boyfriend at a casual dinner.

Things did not go well.

It turns out they went to middle school together. My boyfriend says that my college friend was “a total nightmare” in middle school and “made his life miserable.” This doesn’t sound like my college friend at all.

They were kind of terse with each other at the dinner and afterward my boyfriend was like, “I’m never hanging out with that awful guy again.”

For his part, my college friend didn’t say anything about it beyond that it was a funny coincidence that I was dating someone he went to middle school with. So, I’m not sure if he’s avoiding the subject or he really didn’t have an issue.

Whatever the truth is, I don’t really think these two are going to be best friends, which makes me upset. But now I’m questioning whether my college friend is a bad person. How do I go about figuring it out?

– Friend or Faux

Dear Friend: One would hope that a person changes a lot between middle school and college. It’s all but guaranteed that they will. There’s no telling whether that change is for the better or not but suffice it to say the people who encountered each other in the halls of the middle school and the two people who had a terse interaction at your dining room table are not the same.

It’s probably not worth your time trying to figure out exactly what happened. Take your boyfriend’s word about his experience instead of trying to drum up more evidence. That’s the truth of his past from his perspective. Accept it, acknowledge it, and acknowledge that you can’t change it.

You’re not starting from a blank slate with your college friend. You have years of history from which to form an opinion. This story from his past is another piece of a large mosaic of personality.

It’s not your job to mend the fences between these two, but if it’s bothering you, you can bring the mistreatment up with your college friend (consider checking with your boyfriend first to make sure he’s OK with you sharing everything that he told you). It’s possible the college friend doesn’t remember or doesn’t see things the same way. That’s for them to work out.

But if you want to continue to be friends with him and to be in a relationship with your boyfriend, it may help to just clear the air.

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Dear Eric: I have an ex-son-in-law who is very involved with his daughter (my granddaughter). I support their relationship. He has always struggled financially but recently came into some money.

He has very bad teeth and very bad breath and because of it none of his relationships last more than a date or two.

How can I encourage him to deal with this problem? He is very afraid of dentists. I think it is slowing him down in so many ways.

– Worried About His Smile

Dear Worried: It sounds like you and your ex-son-in-law are closer than would be expected, which is lovely. You have a perspective and opinion on his life, and it sounds like you’re in a position to offer advice. The key with advice is always to determine if it’s welcome and wanted or not.

He is likely aware of his dental problems, and they may be exacerbating his anxiety about the dentist. There are plenty of dental practices nowadays that pride themselves in gentle, affirming care. He may find himself pleasantly surprised. Many of them also offer sliding scale payment or payment plans. You can guide him to these options if – big if – he’s looking for advice.

So, the first step is to ask him, “do you know what you’re going to do with your money?” If he says, “I’m not sure; do you have any ideas?” you have an opening.

However, it might work to be more direct, but still respectful of his boundaries. You might say something like, “I’ve been thinking about how you’re afraid of dentists, but I hate to see you suffering. I have some ideas that might make things easier. Are you open to hearing them?” This last sentence is crucial. Give him the opportunity to consent to hearing your advice before you launch into it. This empowers him and creates a healthier dynamic for a conversation. He’ll be more receptive to your ideas if they come across as suggestions rather than directives.

It’s possible he’s also considering his options and in need of support and encouragement. You could be the push he needs.