How to Stay Open and Expectant During Dating

“Sometimes the good stuff can scare us. It can be more terrifying than our old ways, because it requires us to change.” 

Photo by Toa Heftiba

This time last year, I wasn’t feeling too hot about dating. I shared in Facing the Holidays with Insecurities that for several months I had been getting to know a guy and thought it was progressing to a committed dating relationship. Instead, it came to an end and thwarted any expectations I had about bringing someone home for the holidays. You could say I saw it coming — expected it even. “Of course it was too good to be true. How could you get your hopes up?”  I asked myself. “Relationships never turn out well for you, so why did you expect anything different?” 

Following that situation, I had to do a lot of work praying to Jesus on my feelings of not being good enough to commit to. I had to face the fact that I was struggling because I was basing my worth and value on whether or not a man wanted me, as opposed to placing them in how God values me. While working through my insecurities, I began to see how I let this and past situations further justify what I like to call my “shoe drop” mentality: always suspicious, cynical, and waiting for the shoe to drop so that I could shout “Aha, I knew it!” Without knowing it, I was actually hurting myself as I allowed negative outcomes to control and define my entire perspective about my experience with dating, not leaving space for anything good. 

ALLOWING THE UNEXPECTED TO HAPPEN

A few months later, I went out of town to my church’s Valentine’s Day weekend. That Friday night, a guy strolled up next to me to say hi to a friend I was with. From the corner of my eye, I couldn’t help but notice his loose and curly-ended locks, deep dimples that sat on his cheeks like moon crescents, and a beautiful radiant smile. I discreetly rolled my eyes and said to myself “Uh huh, he’s way too smooth and he knows he’s cute! I don’t have time for games this weekend.” I didn’t even know him and found myself immediately looking for a reason not to like him — trying to distance and guard myself by the negative assumptions I was creating in my mind about him. In some weird way, I was trying to protect myself. I obviously found him attractive, but told myself that someone who looked like he did and had that much charisma wouldn’t take me seriously or be able to commit when the time comes. I had no interest in going down that road. But despite my stand-offish attitude, this guy introduced himself to me, kept trying to make me feel welcome throughout the weekend, and finally succeeded in getting me to hang out with him and some friends that Saturday night. 

When the evening was over, he took me home, walked me to my door and mentioned staying in touch. I questioned if we really would...my spidey senses kept trying to kick in. “He’s just saying that to be nice. And even if he does keep in touch, you’ll talk for a bit, but it’ll eventually fade. Don’t expect anything.” Low and behold, we talked once a week for months. Facing an eight hundred mile distance and the COVID pandemic, we bonded over virtual poetry slams, Saturdays spent talking and laughing on FaceTime, and planning Zoom worship nights together. The result? This man became one of my closest friends and favorite people. We knew we saw something in each other that we wanted and hadn’t seen anywhere else, so we decided to take a leap and try being together, despite the fear of it being too good to be true. 

In the Bible, God tells his people to “Forget the former things; do not dwell on the past. See, I am doing a new thing! Now it springs up; do you not perceive it? I am making a way in the wilderness and streams in the wasteland.” 

LETTING GO OF THE NEGATIVE

Sometimes we think we are so ready for what we want, but when that good thing comes around the corner unexpectedly, it can be hard to recognize and/or accept it because we are looking at the world with broken glasses from our past. We assume we know what to expect. And if we’re honest with ourselves, in some circumstances, we only expect the bad. In order for me to take a leap into this relationship, I had to do some deep reflection. I found that I was still holding on to bad expectations and negative perceptions from my previous relationships with men. Both my past and current unhealthy patterns of behavior had become comfortably familiar. I had begun to expect and accept them from others and myself without even realizing it. They weren’t necessarily what I wanted, but because I expected the same behaviors and pain, that gave me a sense of security and control. And so when things didn’t work out and pain washed over, it made sense. From my distorted perception, everything was the way it was supposed to be. I knew how to deal and navigate through that. Relationship outcomes remained painful, and I was used to feeling deprived — never getting what I needed or wanted after investing so much time, energy, and effort into a relationship. 

However, in meeting my boyfriend, I felt like God was calling me to loosen my tight grip on past pain and misery, to stop expecting the worst from people, to forgive myself and others, heal, move forward, and let the good stuff happen. God reminded me that because Jesus died for me, I was free to no longer sit in a state of cynicism, questioning every nice and genuine thing my boyfriend did and does. God reminded me that every good and perfect gift comes from him, the Father of heavenly lights who does not change like shifting shadows.

Therefore, if God affirmed that my boyfriend was a good choice for me (which he did through fasting, prayer, advice and his Spirit), I could be confident and not second-guess everything. God was also calling me to grow so that I can now communicate my wants and needs and expect good things to happen, while also creating space for an imperfect human being to make mistakes. If I didn’t, I would easily sabotage my relationship, always viewing my boyfriend in a negative light, holding things against him from my past that have nothing to do with him. That perspective would make it hard to look at our relationship in a positive light, and have the grace to see, know, and love him as he is in his entirety — good, bad, and ugly. 

It can be easy to hold onto and expect the negative because it’s what we’re used to. But when we don’t let go, we rob ourselves of the opportunity to create room for the good stuff to happen. We must be brave and break unhealthy patterns that cause us to hurt ourselves and others, and instead allow ourselves to learn new patterns and behaviors that help us build good and healthy relationships. Sometimes the good stuff can scare us. It can even be more terrifying than our old ways, because it requires us to change. It requires us to explore something new, take steps into the unknown, surrender to and trust God. But it’s so worth it. 

If you had told me that over Valentine’s weekend I would meet someone that I’m now head-over-heels about, I never would have believed you. If you told me he would be my best friend, and both a partner and leader in following Jesus, I would have squinted my eyes, looked from side to side, burst out laughing, and asked, “Who?! Where?!” Looking at my past experiences and what felt like slim current possibilities was discouraging. Maybe that’s how a lot of us are feeling right now. We are all facing a pandemic and unable to date the way we used to or the people we used to encounter. But maybe that’s the point - maybe that’s a good thing. 

Can you be brave? Can you choose to leave room and expect the unexpected?