As a child growing up in a household composed of my grandmother, mother and me, I read a lot of women’s magazines.

(Both my mother and grandmother subscribed to several of them and as soon I turned 12, I requested and received my own subscription to Teen Magazine.)

One of the most notable features of these magazines was the inevitable relationship column where readers would write in and ask for advice. One that has stuck with me for all these years is that of a woman who wrote in to ask if it was okay to ask if her boyfriend had ever fathered a child.

Even though I can’t recall what prompted the woman’s question, I do remember the response or the basic gist of it: “Absolutely not! It is none of your business. Doing so is not only incredibly invasive but has the potential to ruin your relationship. For the sake of both of you, keep your mouth shut!”

Despite being very young, I thought that the columnist’s response was a bit harsh. Now that I am several decades older, I not only think it was harsh but downright wrong.

While I am not an expert on relationships and will never claim to be, I have been in and seen enough of them to know that avoiding so-called awkward questions typically ends badly. Speaking from personal experience, some of my most disastrous relationships could have ended sooner or even been avoided had I set aside niceties and asked questions.

I’m not suggesting that the following be brought up on the first or even second date, but below are some questions which should be asked, ideally, right before we get serious with a new boyfriend or girlfriend.

Have you ever had a sexually transmitted disease (STD)?

If there was an award for most awkward question ever, it would probably be this one. No one, not even the most sexually secure people, like to think of their new love interest’s previous partners, but for the overwhelming majority, it’s a fact.

Another fact is that an estimated 110 million people in the US alone have an STD. While many people are unaware they have or had an STD, a surprising number do and fail to inform their new partners. Exact numbers are hard to come by but anecdotally, I know two people who contracted herpes because their respective partners were “too embarrassed” to tell them. (In one case, the man’s girlfriend was afraid he’d stop dating her if she informed him she had the virus.)

Even though many STDs can be cured or, in the case of herpes, be successfully managed, there is still a good reason to ask since some of them, like chlamydia can lead to infertility. While kids may be the furthest thing from either of your minds at the moment, it is still good to know just in case one day the topic of babies comes up. (And for many of us in our late 20s and early 30s, it may come up sooner than we think.)

Speaking of kids, this leads to question #2.

Have you ever gotten someone pregnant or been pregnant? 

Another awkward question, but one that should be brought up for those considering someone as a serious contender for life partner. Much like STDs, unplanned pregnancies are common, and how your partner handled it can tell you loads about them.

For example, one of my friends learned that a man she had been envisioning as her future husband not only fathered a child with his long-term ex-girlfriend but left her when she was midway through the pregnancy because he decided he did not want to be a father. While there were many more details, my friend decided after hearing that information that he probably wasn’t someone she wanted to spend the rest of her life with.

Likewise, I know of at least one case where a woman’s “gentle, understanding” boyfriend flipped out when he learned that she had gotten pregnant as a teenager and opted for an abortion.

Others I know have had children and put them up for adoption without ever telling their most serious partners or spouses.

While this is highly personal, learning what our partner did and did not do if they were ever in that situation, as well as our own reactions to their answers, can give us a lot of insight into the nature of the relationship even if we never find ourselves in that experience.

Do you have bad credit, a lot of debt and/or ever declared bankruptcy? 

This is one that shouldn’t come up unless we plan to cohabitate or marry because frankly, it really isn’t any of our business.

However, once we decide do the former, it does become our business in a very big way. It may not be on the top of most people’s lists, but credit scores really do matter for most of us who don’t happen to be very wealthy and don’t have to worry about money.

Nearly every landlord, whether they list a room on craigslist or advertise in a high end real estate magazine, will probably order a credit report to make sure that a would-be tenant is a good risk. In many cases, when one partner has a terrible credit score or a lot of debt, the other partner will sign the lease entirely in their name which means they and they alone are entirely responsible for the rent.

Furthermore, many people also sign or co-sign for a car loan or other personal loans for their partner which means that they may be paying for their former love’s share of the rent or car long after the relationship ends.

Even if the above doesn’t happen, it’s still important to know what, if any, portion of your boyfriend or girlfriend’s paycheck is going to debt.

Some may grumble that the mere idea of bringing up money is crass and unromantic, but the fact remains that money is the number one thing that couples argue about. Furthermore, we may learn our partner has a “good job” and envision a certain future or lifestyle that has little or nothing to do with reality.

Also, if you happen to be the one with a lot of debt and it causes someone to run, that may be a good sign that this person really wasn’t into you in the first place and only what they thought they could get their hands on. (And lest anyone think I am being sexist, I know just as many men who qualify as “golddiggers” as women.)

In closing, asking or being asked awkward questions isn’t fun, especially when it involves someone we are really into. However, much like going to the dentist, sometimes these things are necessary to avoid a whole lot of problems in the future.

Furthermore, we may not think about it at the time, but answering these questions truthfully can allow for deeper intimacy with our partners. While there are no guarantees, knowing these things about our partners and being able to deal with things we weren’t expecting may actually result in stronger relationships.

Author: Kimberly Lo

Editor: Catherine Monkman

Photos: starmanseries/Flickr; Pasco Olivier/Flickr