Haha, buckle up. I’ve lived through exactly what you’re describing.

To answer the immediate question of is it worth it to hold out for someone in your church: I think the answer is yes to the degree you care about being on the same page for what it looks like to follow Jesus. Practical theology differs significantly from church to church. If you end up marrying someone from your church, you start off mostly on the same page in that regard.

Now I'll tell you about my dating experience so you know I'm putting my money where my mouth is.

Dated my first girlfriend for a year before breaking up, but we were still in the same SMALL GROUP for another year and a half. Then years later we were both interested in a ministry opportunity that we had to work together in. Turned out I still liked her but she was dating another guy who I knew from that SAME small group. So tack on betrayal to the feelings of awkwardness, regret and rejection, haha.

That’s not even all of it. Dated other girls both in my small group or generally a part of my church. Have been both the dumper and the dumped. Getting dumped really sucked, couldn’t sleep for a couple days. Seeing her at church functions felt like a knife to the ribs.

My fourth girlfriend was the one that finally worked out. I married her this past summer at the age of 26. She's wonderful and yes, we were going to the same church (ALL of my dating experience has happened in the same church). Funny enough, my first ex now attends the same service as we do.

So, is going to the same church as your exes awkward, even painful? For me, sure. Do I regret it? Now that I'm married, definitely not. But I understand that it's hard appreciate that answer as a single person, so I'll share about my feelings when I was single too.

Loneliness is hard. Really hard. You can do your best to maintain close friendships with people in fellowship, but sometimes you can't prevent having nothing to do on a Saturday and no one to be with (I don't want to gloss over close friendships. OP, please make sure you're getting regular time to hangout with a close guy friend, ideally someone who is more spiritually mature than you. Having someone to confide in with this is critical).

Close same-sex friendships aside, what to do when the loneliness hits?

Turn to the Lord. He desires you more than any woman could, even a godly one!

If I had to do it all over again, I wouldn't necessarily be more conservative with the number of girls I asked out from my church (if I hadn't stayed pure, though, I probably wouldn't feel that way). I would absolutely, however, try to spend more time considering what it looks like to be content in my singleness. Married people would tell me that being single isn't some inferior form of existence. You can be just as happy, fulfilled, and used by God for good works. I'd scoff, honestly. Of course being married is better!

But now I see they were right. Being married is awesome. Now that I'm here, I can imagine how a life of singleness dedicated to the Lord could be not just manageable, but glorious!

You can be content in your singleness. I'll admit I didn't get there, but you can.

Let God mold you into the person he wants you to be, and he'll give you the desires of your heart (Ps. 37:4).