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Recently Single? What to Do If You Haven't Dated in a Long Time

Andrea has been an online writer for over five years. She's a dating consultant who gives advice on relationships and couples' issues.


Back to Dating after a Long Time

If you were in a long relationship that just ended, you might be wondering how to can get yourself ready to date again. I assume that if you found this article then you want to get back into dating.

I want to help you prepare your heart and mind to get back into the dating scene, navigate technology, and get comfortable on first dates. Let's find someone who is worthy of your time and will appreciate you the way you deserve.

Preparing Your Heart and Mind

My first rule is: make sure you mourn your last relationship. You need to reflect on and process it before seeing someone else, otherwise you'll be trying to process that breakup and meet someone at the same time which can be messy. Sometimes this is unavoidable, as some long term relationships you will process for the rest of your life—consider a 20 year marriage that ended because of divorce or death. That's not super easy to process. You likely have children from a marriage that lasted that long and a lot of history. Someone new will need to respect this about you.

Before you put on the red dress and heels—or the nice suit and tie—you need to do a little bit of self work. Your homework may consist of:

  • Finding a therapist or other professional to help you process the grief and mourn the last relationship. Whether you were dating someone for two years, had a divorce after your partner cheated on you, or you're mourning the death of a spouse, you likely have some memories and pain to unpack. A therapist or other professional can also give you some sound direction and empathy.
  • Get rid of items in your house that are connected to your bad ex. If you dated a guy for a couple of years, and it was toxic, then there is no reason to keep items. Before you date someone new, you need to cut unhealthy attachments.
  • Spending quiet time in meditation or journaling your thoughts. You need to be introspective. You need to analyze your past. If you didn't like your last relationship, then stop and think about why. If you don't want a relationship like that, then don't repeat what led you to that person. It's time for a healthy change. You can do better!
  • Spend a few days just eating ice cream and junk food and watching TV. I recommend Korean soap operas, but not everyone will agree with me. I find romantic comedies are a good way to refresh the heart and help you figure out what you want. Korean soap operas to me are the best for this. You need some lazy comfort days. You need to absorb what are healthy and what are toxic relationships. That way you can make strong decisions when it comes to romance.
  • You need to talk to someone, whether you had a bad breakup or your partner died. Don't try to keep all those thoughts inside of you. Reach out to someone. A real friend is there for you in this time. There are support groups out there. You can find support in person or online.
  • Allow your brain to switch gears. If you still feel really preoccupied by thoughts of your past lover, you may need more time. You need to change your habits and life in order to open up a space for a new partner. You need to deal with raw emotions.

Do Your Homework on Dating Websites and Apps: Be Smart and Safe

When you're ready to start dating again, you may need a refresher on technology and the like. Dating likely wasn't the same as it was five years ago—it definitely wasn't the same 30 years ago. People use apps, dating websites, and all kinds of tricks to fall in love. I like to push people to find potential suitors in person, partly because it gets them more active in their communities.

Dating websites and apps can be tricky and are sometimes unreliable. Don't limit your dating experience to websites and apps only. You'll be cutting off a lot of potential for yourself. If you're scared to find someone and date them in the real world, do you think it'll get easier when you have to interact with that person outside of technology? Don't psych yourself out, okay?

My preference always has been to date people in person rather than online, but of course, a lot of people find love digitally. Just don't use online dating as a crutch.

Try Dancing

If you haven't dated in awhile, one of the best things to do is try social dancing. Look for a place in town where you can take dance classes and meet people. This is a good way to get out of your home, on your feet, getting some exercise, and potentially into the arms of someone really attractive. Dance communities also help people develop friendships and form bonds with others.

Look for other community oriented places in your area. People do still find dates at bars, churches, parks, libraries, museums, etc. Follow your interests and you'll find someone who has similar interests. That's already a good place to start when it comes to dating.

Also, if you're not really sure you want to date anyone, exploring your city is still good for you. You can be single and mingle, and you can be single and still hit up the art galleries. It's also good to go to different community events to sharpen up your social skills. Practice having conversations with strangers. Improve your charisma so that you can be a better date. Observe others.

Often times when we partner up, we don't meet up with friends and acquaintances as much. We can become insular about our social skills. When you are around more people this can help you to learn new communication methods.

Someone Will Get You


Avoid Online Scams

For those of you that are going to use online dating and apps, I recommend that you do your homework. Keep a close eye on subscription fees. I would avoid paying for services. Make sure you read reviews. There are a lot of scams out there on dating sites and apps, so you need to be careful and in the know.

Never send money to someone you haven't met. If you just started seeing someone, don't send them money at all. They may be fishing for rich people to cover their butts. Be very careful with your wallet. Don't make a big financial investment in someone early.

A woman I know dated a man online and things went downhill pretty quick. He realized she was recently divorced and wanted her alimony to pay for his new laundromat. That should scream fishy to you.

Also, don't get catfished. If you click with someone online, make sure you have a video chat with them. If the person only wants to text you and send you pictures, this could be an indication that he is hiding something. You could be getting catfished. You need to authenticate in some way that the person is real and who they say they are.

If it seems too good to be true, then it probably is. People use fake pictures and info to scam others. There are bots out there to phish information out of you. Don't offer personal details about yourself, especially credit card info or your social security number. Don't answer the question who was your first kiss or the name of your first pet. Don't answer questions that are security answers for your banking information.

Often bots or scammers have really bad grammar, so unless there is a good reason that their sentences are so funky, drop them. Maybe even report them to police or report the website to the BBB.

You need to be careful. Read up on dating sites before you join them.

Enlist Your Friends

Have someone help you put together your online profile. Sometimes it can be overwhelming to piece together the right profile. Having second eyes will ensure that you pick the right pictures, the right interests, and the right words to get someone worthwhile into your life.

What you might think is great about yourself might not necessarily be the best way to advertise on a dating profile. Your friend will help you figure it out.

Your friends will also likely have good dating tips for you if they've been doing online dating for awhile. Try to lean on other people's experiences so you can skip the bad mistakes. Your friends might have some good recommendations for websites and apps. They might also be able to fill you in on who seems like a good date from a website and who looks terrible. Your friends can help you save time rather than waste it.

Your friends could also help hook you up with another single person they know. Your friends might know someone who is single and also looking. They can give you a heads up of what the person is like. Couples often get setup together from a mutual connection. What's nice about this is the person comes with a reference and the person has been vetted.

Ask your friend lots of questions about this potential person like how they met, what are her interests, why you think the two of you would be a good match, have them show you a picture, get an idea of their dating history.

Love Is around the Corner


First Dates

When it comes to the actual date, don't worry if you need a refresher.

Try not to make a big deal out of the first date. Try to be warm, charismatic, engaging, and not too serious. Maybe use some extra deodorant if you sweat under pressure. Try to relax and be yourself. Be genuine and honest.

Don't repeat the same things over and over. If it's been awhile since you've been on a date, try to say that once. You want to focus on the other person and give them your undivided attention. Don't focus so much on the fact that it's your first date in a really long time. The other person likely doesn't need to know that.

People tend to get second and third dates if they make the other person feel good, if they engage in interesting conversations, and a little bit of luck. (You want to setup yourself so you have space for good luck.)

Where to Go

I recommend for a first date to go somewhere on an afternoon weekend. Look for charming things to do that might help break the ice: check out an orchard, check out a new place, go to a new coffee shop, check out a downtown area you've never visited, go to a museum, go to the botanical gardens, maybe go to winery if you both like wine.

I recommend somewhere that is public and where you can walk and get a feel for his or her pace. Also, if you start in the afternoon you can get a feel for the person and decide whether you want to advance things to dinner—and what kind of dinner. Don't go somewhere super fancy just yet. Pick some local and authentic with decent pricing. Also, pick something that isn't too out of the way. (Don't pick fast food unless you are trying to put this person in the friend zone.)

Starting a date in the afternoon gives you enough time to figure out what you want to do. Have an excuse ready if you need to jet out of the date, but also schedule plenty of time for the date in case things do go well.

What to Wear

Wear something nice but not over the top. Nothing too flashy. Something YOU feel comfortable wearing. If you have a hard time walking in heels, skip them. I recommend wearing a nice solid color like blue or green. Plan your outfit in advance.

  • Consider the season, the activities planned for the day, and what helps bring out your best features.
  • Don't wear something old, raggedy, or with holes; avoid looking like a general mess.
  • Don't wear loose or ill-fitting clothes.
  • Don't wear clothes with tricky pieces or unreliable zippers and buttons. Avoid the embarrassment.
  • Don't load up on the jewelry.
  • Do style your hair.
  • Wear nice shoes. They don't have to be your best shoes, but don't wear your worst shoes.
  • No jeggings.
  • Avoid see-through clothing.
  • Don't wear something strapless. You might regret it.
  • Avoid clothing that has words or odd sayings. Worse than that: clothes with inappropriate words.
  • Get rid of dog or cat hair.
  • Clean up your nails. File them. Make sure they're clean.
  • Brush your teeth. Carry some mints. Avoid garlic and onions.
  • If you wear glasses, make sure to clean them before the date. Get rid of any gunk, dirt, or dust.
  • Most people can't rock hats. This isn't a good time to see if you can rock a hat.
  • Check the weather and prepare accordingly.

What to Say

While on a first date you want to keep things fun, interesting, and engaging. You want to come off charismatic, smart, and sharp. You don't want to be quiet the whole time and challenging to interact with. If you're too quiet you'll come off uncomfortable—and if you really are uncomfortable, try to get out of the date sooner than later.

  • Don't talk about controversial topics.
  • Don't steer the conversation into too much politics or religion. However, if you have similar views, this is safer ground.
  • Don't talk solely about your past relationship. You'll seem like you're stuck on the past person and still in love with them.
  • Do talk about your interests, what makes you happy, things you recently learned, or highlights from your week.
  • Prepare a list of questions and ice breakers in your head.
  • Do comment on things you see around you like pretty flowers, nice art, and the weather. This is why going to an art museum is a good idea.
  • It's okay to talk about your kids or pets, but don't dominate the date by bringing your favorite people up. Often, if you have kids, then whoever you're dating also has kids or pets, so you can bond over this.
  • Keep things fun, not dour.
  • Ask about what they do in their free time and some of their favorite things about the city.

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