Somewhere between the first date and shopping for an engagement ring lies a land teeming with adventure, discovery, and many unanswered questions. We get it. We’ve been there.

So we compiled a list of 10 questions guys commonly ask and our best answers to these often tricky (and awkward-to-talk-about) situations. We hope this helps you rest easy and enjoy the adventure of your new relationship.

Do I always have to pay for everything?

“Who pays?” is an increasingly difficult question for many guys to handle. Approach it incorrectly and we risk falling somewhere between a chauvinist pig and a freeloading good for nothing.

While you don’t always have to pay, you should be able and willing to. When you pay you:

  • communicate value.
  • establish a pattern of servant leadership.
  • learn to put her needs above your own.
  • are reminded of the costs associated with caring for another person.

If your girlfriend wants to treat you to a nice date, by all means, accept her gift. After all, who pays for what is not nearly as important as the attitude the use of money exposes. Talk to your girlfriend and discuss expectations.

If you are unable to pay, consider if you’re trying to impress her with outings beyond your means. If so, don’t be afraid to scale your plans back. A picnic can be just as much fun as an expensive dinner.

Can I keep my female friends?

It is possible to maintain close opposite-sex friendships, but there must be clearly understood boundaries in place to keep anyone from getting hurt.

Physical attraction is more fluid than most people think. Just because you are not attracted to a person today, does not mean attraction will not develop tomorrow. Most people who cheat don’t see the attraction building until it is too late.

Avoid spending time alone with other girls and talking about personal matters. This can create emotional bonds. Save those conversations for your guy friends.

Talk openly with your girlfriend about boundaries you both want to set up and why. Remember, this isn’t about controlling each other’s friendships as much as it is figuring out the best ways to honor and protect your relationship.

How do I know if she is REALLY a believer?

This is a foundational question, but it can sometimes be the hardest to determine. Some people just know all the right answers, especially if they’ve grown up in the church. While you don’t want your conversations to feel like an interrogation, you’ll need to keep investigating until you can uncover the truth.

Whenever you bring up God in your conversations, notice how she reacts. Is she receptive, or does she go into her shell and change the subject? Do her behaviors match her stated beliefs?  Can you see any spiritual fruit? Does she love others well? Is she growing in her faith?

Keep in mind there is a difference between knowing things about Jesus, and being a follower of Him. (See James 2:19)

How do I deal with clinginess?

In the early days of the relationship, it feels good to have someone need us. It validates our worth. The problem is our earthly relationships were never meant to determine our worth or fill all of our needs. Only God can do that. When someone starts looking to you as the answer to every question, there’s a problem.

If you are asking this question, it may be a sign you are being asked to fulfill a role you were never designed to fill.

If you sense that is the case, try gently encouraging her to strengthen her relationship with God and with other girls. Joining a women’s Bible study could be a way for her to achieve both of those goals. As she learns to rely more on God and other women, you may notice the feelings of “clinginess” decrease.

Sometimes however, what looks like clinginess is just an attempt to show affection. Your girlfriend may simply speak a love language you are not familiar with. If that’s the case, thank her for her efforts, and talk to each other about the ways you most feel loved.

And if you’re the one who’s clingy, these same principles apply to you. (Except, no, you cannot join a women’s Bible study.)

Is she the one for me?

This is an important question to ask and one you will want to keep asking as your dating relationship progresses. While there is no such thing as a “perfect match,” the overall trajectory of your lives should be heading in similar directions.

For example, if she doesn’t want to get married one day, then should you really be dating her?

Also, do you want to have kids, but she doesn’t? Do you crave an adventurous lifestyle while she thrives on routine? What if she feels called to be an overseas missionary, and you have absolutely no desire to do so?

It can be difficult to address possible barriers to your relationship, but it is wise to think about these things and process them with her. If your lives are heading in different directions, it’s better to find out sooner rather than later.

Calling Men to Courageous Manhood

Can I still hang out with the guys?

You’ll (inevitably) find yourself spending less time with your friends now that you’re dating someone new. It’s natural. The important thing is to let your friends know that even though some things might change, you still value their friendship. It will be hard to have a successful, long-term relationship with your girlfriend without their counsel and support.

Talk to your girlfriend about what a guys’ night might look like in your relationship. If your girlfriend gets along with your friends, even better! Hang out as a group sometimes.

What if my girlfriend doesn’t like my friends?

Spend time with your buddy, and you have a fight with your girlfriend. Avoid your buddy to keep the peace, and you can’t shake the feeling that a small piece of you has died. No one wants to be in a position where they have to choose between a longstanding friend and a girlfriend, yet sometimes that’s what it feel like. What do you do?

Much of this depends on your ability to listen well and not get defensive. You will need to discern if her objections are motivated by excessive clinginess and jealousy, or if she sees something in your friends that you can’t.

Remember, God created Eve to be Adam’s helper. There is a chance your girlfriend is simply trying to live out that role and help you be your best. Look closely at your friendship.  Does spending time with your friend bring out your best or your worst?  Does it help you become more like Christ or cause you to compromise your integrity?

If she’s wrong in her assessment, encourage her to spend time with you and your friend to get to know him better. But if she’s right, have the courage to listen to her advice.

How do I resolve conflict with my girlfriend?

The best way to handle conflicts is to:

What are some red flags I should watch out for?

Everyone has conflicts. What matters is how you handle them. Name-calling, disrespect, hurtful insults, threats, and physical violence have no place in a relationship. Arguments should not be won through force or manipulation. Even if your girlfriend shows remorse, be careful. Such behavior usually only gets worse over time. If you don’t see her remorse lead to change, it might be time to rethink the relationship.

When do we talk about the future?

Talking about your desires for the future is a natural part of getting to know each other. So go ahead and talk about career goals, where you would like to live, and if you see yourself with a large family one day. All of these are fine. The only time conversations like these get awkward is when one person begins to feel cornered into making premature commitments.

Remember, your purpose in these conversations is to know each other better, not to push the relationship to move faster than it should.

How do I know if I should break up with her?

There are many reasons you might break up with someone: faith incompatibility, red flags, bad timing, communication issues, behavioral problems, cheating, or even a simple lack of interest.

It can be hard to face this kind of decision, but it’s important to explore your doubts. If this is not a good relationship for you to be in, it’s better for you to figure that out now rather than later down the road.

If you’re unsure, give yourself time to figure out what you want to do. Talk to your friends, family, and God about your doubts and concerns. Don’t let the fear of being alone keep you in a bad relationship.

Breaking up may feel like a catastrophe, but dating is very different from marriage. You don’t need to feel like you should have made it work. If it doesn’t work, it doesn’t work.

Remember, dating is about investigating if this relationship has a future. If you no longer think it does, it’s okay. You gave it a shot! You can walk away with integrity.

If I decide to break up with her, how do I do it well?

It may be one of the hardest things you’ve ever had to do, but it’s important to show you respect her enough to talk to her in person. Never break up with someone over text. Even if she has hurt you, you want to be respectful toward her.

Before having this conversation, try to give her some indication you’ll be talking to her about something difficult. It may not seem like much, but do your best to affirm her during the conversation.

Being rejected is hard! And being the one to break the heart of another is hard too. Be honest with your reason for the breakup, even if that reason is simply your feelings aren’t there anymore. Whatever it is, own it. Give her time to respond to what you are saying and offer as much closure as possible.

When it’s over, let it be over. Continuing to text and hang out together may seem like the kind thing to do, but it will only serve to draw out the pain. Besides, getting married one day and still being friends with every girl you ever dated is asking for trouble.


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