These two category is not an easy match.
1. Just because they don’t have the same experience as you, don’t rule them out.
A failed marriage can feel like a badge of honor and you might want to choose people who have been through that same experience, which is fine. But then you might find yourself on date #1 sharing how each of your marriages imploded and not spending precious time getting to know each other in real ways.
Divorce changes you. It re-shapes you and your life in drastic ways, but it doesn’t have to define you and be all that’s on your mind and in your mouth. If it is, you may need to take a break and re-enter dating when you’ve gotten whatever space you need to process what happened.
But if you’re feeling good about where you are and are ready to be open to someone new, don’t cancel a date just because someone hasn’t been married before. If they’re dating, 100% of their past relationships have failed too, and failure doesn’t have to be your common bond to build something anew.
2. Go slow
Someone who has never been married likely hasn’t read all of the couple-y books. They probably don’t know their own love language, and they may think you’re talking about something inappropriate if you mention keeping your “love tank full.”
Since you’re used to being married, you likely won’t have a great memory of what things were like when you were just starting out, but you probably didn’t tell your ex-spouse on your first date about how traumatic it was that you didn’t make the cheer squad in middle school and your parents shamed you for it. You need to go slowly and share yourself bit by bit. It’s an adjustment since you’re used to sharing everything with one special someone, but you get to re-learn yourself in the process.
What do you like to do? How do you feel about your job? It’s new and exciting to get to be able to ask and answer questions like those.
3. Be prepared for a learning curve.
If you were married for a while, you might be unprepared for the single world that has developed while you were committed. Your never-married may have been in the single world much longer than you. They may have been actively dating, or since they weren’t married, closer to their single or actively dating friends. They might have certain expectations that you won’t understand at all.
This is 2019 and the world of dating has changed a lot. You may have never heard of ghosting or curving, but if you keep dating, both will probably happen to you. Be prepared to stumble and fall along the way, but make sure to pick yourself back up and try and try again.
4. Be prepared for them to have a learning curve too.
You’ve had a spouse, so you likely have expectations about what that means. They always buy you flowers for special dates or they are the person you cuddle with in front of the TV every night. Someone who has never been married may not have those same relationship ideals. They may not even had many long-term relationships or ones that developed the level of intimacy that most people expect they’ll get with their spouse.
Just as you would in any situation, you’ll need to teach your partner how to be in relationship with you and what you want that to mean, and give them a little grace while they catch up.
5. Be prepared that they may want things you’re not open to.
Someone who has never been married, even if they’re in their 40s, may still be open to the traditional route. They may want to get married and have children. You may already have children from your previous marriage, and you may not want any more. That would be something for you to think about it and tease out if they’re someone you like. This is where it’s important for you to be clear about what you want and don’t want, and if it’s not clear to you yet, be upfront about that with them.
While many of us probably wouldn’t want to sign up for a race that would include the chance of getting mud up to our eyeballs, there’s a lot of pride that comes from taking a chance and completing something. Re-entering the dating world is just like that. You’re putting yourself out there and showing that you love yourself enough to know that there is someone out there that can love you just as much. Just because you were married before and it didn’t work out doesn’t mean you are incapable or unworthy of love. It just means you have to do some more work to find it. In the meantime, learn to give anyone a chance—even if they are a bumbling never-married—because they might be the key to your second chance at happiness.