When starting a relationship, ask your boyfriend about his family relationships, previous breakups, communication style, and sexual history. Also, ask what he likes about you beyond physical appearance.
In the early stages of your relationship, you should ask your boyfriend about his relationship with his family members. Find out how he gets along with them. In particular, you will want to know how he feels and treats his mother and sisters (if he has any). If he treats them with respect and love, and he genuinely appreciates the characteristics that make them unique, that’s a good sign for you. If he displays a rather chauvinistic attitude and you don’t like traditional male-female roles, you might do well to run the other way.
When you ask your boyfriend about his family, he may respond that he is estranged from one or more of his family members. This doesn’t necessarily mean he’s a bad boy or a poor fisherman. It could mean that he has been the victim of abuse, both physical and verbal; it could mean that there were so many differences that taking some time away from each other was the best thing to do. Be careful, however, if his family relationships are frozen due to his own intolerance. If he gets upset, angry, or disgusted when a family member doesn’t do things the way he expects or wants, you can bet you could get the same treatment.
Another important question to ask your boyfriend is how his previous relationships ended and why. You will need to know what he considers unforgivable in a relationship and what he considers are good reasons to break up. It’s a good sign if your boyfriend takes at least a small amount of responsibility for the breakup of some of his past relationships, as it’s unlikely that he’s always done everything exactly right. It’s also nice if he has something good to say about at least a couple of his ex girlfriends. If he spews hatred at everyone, this could indicate an anger problem.
Ask your new boyfriend how you can expect him to act if he’s angry or disappointed. Ask him if he’ll be forthcoming about what’s bothering him or if it’s more his style than him to keep it quiet and bottled up. It’s a good idea to encourage him to communicate openly with you about his feelings about him, even when the topic is unpleasant. Good communication can be the difference between a relationship that lasts and one that burns down rather quickly. If he says anything that indicates he’s overreacting in a relationship, you should strongly reconsider having him as a boyfriend; run to the other side.
If you plan to get physically intimate with your boyfriend, ask him about his past sexual relationships. You don’t need all the gory details, but you’ll want to ask your boyfriend if he’s had many sexual partners and if he’s always taken precautions to prevent STDs. If he hasn’t always worn condoms in the past, you might suggest getting tested for STDs before having sex with him. Regardless of the outcome, however, it’s important to remember that using condoms can give you a good level of security from STDs, and they’re a good idea until you’re 100 percent sure that your partner is STD-free and he is, and will remain, in a monogamous relationship with you.
Last but not least, ask your boyfriend meaningful questions about what he likes about you. Sure, he’s very nice if he thinks you’re beautiful and he finds you physically attractive, but you also want to know what he likes about your personality. After all, you want to know that your boyfriend will still like you on one of your most horrendous bad-hair days. You also want to know that he appreciates you for all the little things that make you unique.
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