Questions to Ask Your Boyfriend

Whether you're experienced at playing the field or you're just diving into the dating pool, there are questions to ask your boyfriend—both serious and fun. Whether you address it as a heart-to-heart, a getting to know you chit-chat, or a game like Truth or Dare or Twenty Questions is up to you. Choose the method you think he'll respond best to and maybe he'll ask you a few questions of his own.

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The Fun Questions to Ask Your Boyfriend

Before you get into the heavy stuff—when your relationship is pretty fresh and you're not quite serious—it's nice to get to know the silly basics of what makes your man tick. What's his favorite color? Which food does he absolutely despise? Can he beat you in a game of Monopoly? Here are some fun questions to ask your boyfriend:

1. What's your favorite color?
2. Favorite board game?
3. Describe yourself in a single word.
4. Describe me in a single word.
5. Would you go dress shopping or shoe shopping with me?
6. Another girl hits on you in front of me. How would you handle it? What about if I wasn't there?
7. What is your favorite body part?
8. What song reminds you of me?
9. Do you think we've met before in a previous life?

The Heavy Stuff

Once things start looking like they're getting serious—or physical (or both)—it's a good time to start asking the more personal questions. If you're inexperienced at dating or you're pretty shy when it comes to asking potentially awkward or embarrassing personal questions, it may be incredibly intimidating to dive right into a conversation of this sort. However, there are reasons you should:

• Protect your heart. By the way he answers your questions; you may determine he's a little bit of a heartbreaker. Is he in it for the long run or are you a fling for him? Does he feel as strongly about you as you do about him? You don't even have to have a "So…where is this relationship going" talk with him (that tends to scare men off sometimes!) to find out what you need to know. How did his last relationship end? Are he and his exes still able to be friends?

• Protect your health. As far as your health goes, you need to know how many partners he's been with (or at least whether he used protection every time), if he's been tested for STDs, and how many times he put himself at risk for an STD by not using protection.

• By asking the heavy questions, you can see how comfortable you really feel with your partner and how well you two discuss uncomfortable topics. Being able to talk about anything is a sign that a relationship has a strong foundation.

Questions to Ask

1. How did your last relationship end?
2. Are you and your ex still friends?
3. How many partners have you had? (This one's optional…if you don’t want to compare numbers, don't, but at least make sure you know he was safe with each of those, or has been tested for STDs since then. Some symptoms don't show up in men, but can be detrimental to a woman's ability to reproduce if passed along.)
4. Have you put yourself at risk for an STD by skipping protection?
5. Have you been tested for STDs/HIV?
6. Would you be willing to go in for testing again before we get more involved?

If your relationship's not that new and you've already talked of marriage, here are some more biggies to ask before getting engaged:

1. Do you want kids? How many?
2. Where do you want to live in the long term? City? Mountains? Country?
3. What are your retirement plans?
4. What is your philosophy on money within a marriage—is what's yours mine and vice-versa, or will you prefer separate accounts and a roommate situation with bill paying?
5. How do you feel about taking in family members during a hard time? Elderly parents?
6. What's your take on getting the housework done if both partners work outside the home?

Processing What You Learn

Try not to jump to any immediate conclusions during your question and answer episode. Instead, take a day or two to think about all the answers as a whole. Go back later with more questions for clarification if necessary. Maybe he did cheat on his last girlfriend, but was he sixteen when he last had a relationship? That's not so bad if he's now a more mature twenty year old who learned from his mistakes. Get his answers in context, then mull over them to decide where you want the relationship to go.

Warning: if he seems pretty casual about the sexual questions, meaning he's been with a significant number of people in the past year and wasn't as careful as he should have been to protect himself, that's a red flag. Look for cues that he doesn't take his health seriously when it comes to sex, because he won't take yours seriously either.

Want to chat with fellow LoveToKnow visitors about your dating and relationship experiences? Come visit our Dating forum!

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