The Homeless and Your Dating Relationship

how to serve with your boyfriend

I was nervous as we pulled up to the apartment complex. My boyfriend got out of the car with me and we walked up to meet my friend, Roy. Roy is a recovering alcoholic who has been homeless in the past, but is now in housing. He’s also one of the most faithful Catholics I know and has a heart for our Blessed Mother. He’s a little shaky on his feet after being hit by a car as a pedestrian several years ago. We met when I was a missionary doing homeless outreach and have stayed in touch ever since.

My boyfriend gently grabbed hold of Roy’s elbow and walked him to the car door. Each of them had heard plenty about the other. I was eager for my boyfriend to meet someone so important in my life, and nervous and hopeful that Roy would approve. This meeting was in some ways more important and more telling for me than my boyfriend meeting my parents.

I dropped the two men off at the park where we were headed to meet some other homeless friends and missionaries for lunch. I held my breath and hoped the two men had something to talk about. When I walked up after parking the car nearby, I let out a sigh of relief to see them talking and laughing.

I was so grateful for my boyfriend coming to meet Roy and several other homeless friends with me. My boyfriend commented that he loved seeing that part of me and watching me come alive in that setting. It’s one of the best compliments he’s ever given me.

Important Discussions During Dating

In the early stages of a dating relationship we may talk about our family upbringing, what we’re looking for, and so on.

As things get more serious, old wounds might be covered, how you’d like to parent children, and more.

But what about a conversation about the homeless?

Do we ask our significant other how important serving is? What are his default assumptions about homeless people? What about tithing?

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Serving the Poor is Not Optional in Your Vocation

Several years ago, I had the opportunity to serve with a ministry in Denver, Colorado called Christ in the City. Around 25 young people make a commitment for a year or two years to live together, receive formation, and walk the streets daily looking for homeless people to talk to.

So after serving the homeless for two years and having ongoing friendships with many of them, maybe I’m biased. But then again, maybe the Church is, too.

Serving the poor in your marriage is not optional. It’s part of the wedding Mass, and the poor that your family has served will be the ones who welcome you into eternity.

The first option for the final blessing of a wedding Mass is as follows:

May you be witnesses in the world to God’s charity, so that the afflicted and needy who have known your kindness may one day receive you thankfully into the eternal dwelling of God.


Are we practicing in our dating relationships the care for the poor that we would like to have as part of our family culture?

Ways to Serve the Poor and Homeless in Your Dating Relationship

Here are some ways you can incorporate serving the poor into your dating relationship.

See what ministries are in your area.

Are there local food banks that serve the homeless? If so, try to not just serve the meal, but also to sit down with the guests and share it with them.

Be bold in reaching out to strike up a conversation. It may be awkward at first, but they are likely going to be grateful for a kind word and someone to listen to them.

Be prepared to help.

Make a habit of rolling down your car window when you see someone who’s homeless on the street corner. Keeping socks, water bottles, or soft granola bars (for those with teeth problems) in the car can be an easy conversation starter (check out these Blessings Bags for more ideas).

But if you don’t have anything to offer, be not afraid! Say hello and ask the person’s name. Offer to pray for them and be sure to follow through.

This is hard for me, even after two years of daily accompanying the homeless. There’s a fear of awkwardness. What if they just want something from me and don’t want to talk?

But take courage! This can also be a vulnerable interaction between you and your significant other. If he thinks it’s silly to just say hello, this might be a good conversation starter. Or if you’re too afraid, ask him to be brave the first time and start the conversation. See if you can call each other on to notice the homeless more, to smile, make eye contact, and recognize their dignity.

Pray for the poor.

It could be part of your prayer before meals to pray for those who go hungry and those who are lonely. Remember the names of the homeless you meet while serving or driving and pray for them. And ask them to pray for you.

What a gift it is to entrust someone, who maybe doesn’t receive the trust of many, with your intentions.

Make greater sacrifices.

Think about making sacrifices in your spending and use that money to tithe as a couple. Maybe it’s not going out to eat one Saturday during the month, and setting aside the money you would normally spend on dinner. Or making coffee at home and enjoying it on the front porch instead of at a coffee shop.

These little sacrifices help us get into the rhythm of thinking more of the poor, maybe even more so than a direct withdrawal to a charity.

These tips can also be practiced as a family if you’re already married and help to encourage your kids to think often of the poor.

Let’s be bold in reaching out to those most in need through our kindness and prayers. Hopefully, we will have the joy of one day being greeted by them in eternal life.

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Makena Clawson served with Christ in the City from 2015-2017. She enjoys speaking Spanish, painting little gifts for friends, and hearing people’s stories.

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  • Reply
    The Homeless and Your Dating Relationship | Learn Relationships
    May 15, 2019 at 5:19 am

    […] One woman shared her experience of how serving the homeless deepened her relationship with her boyfriend and brought them closer to their … read more […]

  • Reply
    May 15, 2019 at 12:51 pm

    Makena, this reflection is outstanding! I was especially stunned by the final blessing you pointed out! It’s amazing to have people like you help us think about such daily but forgotten topics.

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