The Single Dad Reboot

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7 Tips for Dating After Divorce

I still remember the very first date I had after my divorce. Honestly, I’m not sure I’ll ever forget it. It took a long time to get to the point where I felt comfortable enough to go on that first date, but even then, I was still questioning whether I was ready.

The anxiety, nervousness, and curiosity about whether I’d crumple into the fetal position when faced with questions about my divorce and thinking too far ahead into the future of a potential relationship almost got the best of me. After all, it had been about ten years since I had been on a date. I didn’t even know how to “date” anymore.

I took a deep breath and told myself, “It’s only a drink, and you aren’t a social buffoon. It will be fine”. And off I went into a night of hope and possibility.

Love at First Sight?

No, it was not love at first sight, but everything went fine on that date. We went on a few more dates. But, looking back, I could have handled some things better with the person I went on that date with. I also could have avoided some other post-divorce dating pitfalls as well. Although this is geared more towards those sliding back into dating after divorce, these are probably good tips for anyone getting into dating in general….

  1. Be Clear on What you Want

As humans, we long for love, connection, and intimacy. It’s on Maslow’s Hierarchy of needs right in the middle. That doesn’t mean dating must always be about looking for your lifetime partner. If you are dating to find your life partner, make sure you know what you want in a partner. I’m not kidding when I say write a list of EVERYTHING you are looking for in a partner. This list is not static and will probably change, but you should understand what you want.

On the flip side of the coin, and I’m not judging, sometimes we want something casual. Whatever you’re looking for, you must be honest about what you want. Look, it’s 2022, and you can find someone for any relationship or dating situation you might be looking for. Yes, some will be harder to find than others, but it will be even more complicated if you aren’t clear on what you want. It’s a waste of your time and the other person’s time if you try for a fling with someone looking to settle or with someone looking for a fling.

When I started dating again, I wanted something more casual, but I wasn’t honest with myself. By simple, I’m not referring to sex, but I had a skewed view of relationships due to how my marriage ended. I needed to go slow, take my time and feel things out to see what I could handle emotionally. Instead, I escalated too fast, led a couple of early dating partners on, and realized I had gone too far too quickly and ended up hurting people. That was all my fault for not being honest with myself or the people I was dating.

Yes, getting hurt and hurting others is a part of the game, but it doesn’t mean you shouldn’t treat people with respect and dignity, which leads me to #2.

2. Be A Good Ender

If you aren’t feeling it with someone, tell them you aren’t, especially if you have gone on multiple dates. It’s even more critical if you have been intimate. Don’t ghost people. In this age of text messages and social media, it’s easier to avoid the situation and disappear but grow up and face the conflict. It would be best if you told someone that you don’t see things working out or don’t think they are a good fit for you. Yes, it will probably sting them because it never feels good to get rejected, but at least they know it’s over, and you can move on with dignity.

If you disappear, you leave that person with questions about themselves. It also makes you look like a jerk. I’m not going to lie; I have done this in the past and had it done to me. It sucks. If you happen to run into the person again, it makes for a super awkward and uncomfortable conversation. Please do the right thing and tell the person it’s over.

3. Date the Type of People You Normally Wouldn’t

Everyone has a “type.” But guess what? If you’ve strictly stuck to your type and you’re single, your “type” isn’t working for you. Try something different. After your divorce, you are in this miraculous place where you start from scratch — a clean slate.

I get that you can’t control what you are attracted to, and attraction isn’t a choice. But if you give people a chance, you might be pleasantly surprised by what you find. Sometimes we overlook someone due to extenuating circumstances like being irritated by the day we had, being hungry & tired, or just being in a closed frame of mind for some reason. But if you put yourself around the same person in a better mindset, you might feel different.

Try dating other people who you usually wouldn’t. Just meet for a drink and get to know someone. Dating, although frustrating at times, should be fun and about finding out what you like and don’t like. You can learn something new from everyone you meet. You can find a new hobby, meet new friends, build your network, and, most importantly, develop your social skills.

I went on quite a few dates that didn’t extend past the first date, but I ended up having fun, meeting some incredible people, and learning new things. All I did was go into every date with an open mind and look to have fun with no other expectations.

4. Be Careful with Friends of Friends

I learned about this one the hard way. One of the easiest ways to find people to date is through friends of friends. Your friend’s wives or husbands will probably have someone they think will be PERFECT for you!

Of course, there is absolutely nothing wrong with having a friend set you up with one of their friends. Just be mindful that if you treat that person badly or things end badly between you, it could strain your relationship with your friend, your friend’s husband, wife, or whoever set you up. You’ll most likely run into the person you were set up with again, which can be awkward if you don’t behave respectfully. So, an important life lesson, treat people with dignity and respect, and be a good ender!

5. Take Red Flags Seriously and Listen to Your Gut

It’s a story as old as time. You start hitting it off with someone and immediately ignore any red flags. Either because you don’t think they are a big deal or you want to give someone the benefit of the doubt. Red flags continue to pile up; the relationship ends badly, then you wind up kicking yourself for ignoring obvious red flags.

Or everything seems too good to be accurate, but you have this weird feeling in your gut that something isn’t right. You ignore that, then months later, your heart is broken when the “truth” comes out because you didn’t investigate what your gut was telling you at the beginning.

Nobody is perfect. We all display red flags in some shape. Sometimes you get a weird vibe, which turns out to be nothing. Each situation is different but should be taken seriously. If red flags are piling up, it’s a sign to you to hit the eject button. If your gut is telling you something is off, investigate it. I’ve ignored both and suffered heartbreak because of it. Ultimately, I could only blame myself for disregarding what was right there in front of my face.

6. Be Patient and Take Your Time

Coming out of a divorce, dating will be a marathon, not a sprint. For the “just-dating-out-of-divorced” crowd, you don’t need to enter a relationship with the first person you date. You will most likely feel the magnetic pull to do that because it feels “natural,” but that is because you are coming from a marriage. You’ll probably go through periods where you will be all about dating and periods where you will hate it and take time off.

If you have been working on yourself to heal and improve, you will backslide into your old ways that you are working to change. It’s natural. Growth is not linear.

Be patient and take your time. You will have to go on some bad dates. (It is fun trading dating war stories with other divorced people you meet.) It might take some time to find someone you connect with. Get out there and explore. Try new things. See what you like and don’t like. You don’t have to jump into a relationship right away.

7. Focus on Fun at First, Not the Future

When you first start dating again, you’re probably going to have many thoughts about, “maybe this is the one!” or “I hope we hit it off!”. I found that line of thinking just made things worse for me. The anticipation made me more anxious and nervous. Eventually, I switched my mindset: “Regardless of what happens tonight, I just want to have a fun night.”

“Fun” can mean many different things, obviously, and I’m not referring to it in the sexual sense here. In my case, it was based on fun conversation. Maybe meeting up at a place I had never been to. I might try some new activity I had never tried. I could even be going to a different part of town. I just tried to focus on having a good time with no expectations or strings attached.

If I ever tried to put more weight on things than that, it would be a dud of an evening.

Everything is going to be okay, and you are going to be okay. The anxiety and nervousness the thought of dating gives you are natural. Even if you were married for a long time, it doesn’t mean you can’t find love again. If it has been a while since you’ve dated, it will take a little while to adjust to the times, but you will.

Don’t give up; you will find what you are looking for. As the saying goes, it will happen when you least expect it. That will make everything worth it.