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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.

Dating can be tricky, especially if you haven't been with someone in a long time. If it's the right person, things will fall into place.

Dating can be tricky, especially if you haven't been with someone in a long time. If it's the right person, things will fall into place.

Back to Dating after a Long Time

If you were in a long relationship that just ended, you might be wondering: how can I start dating again? Should I browse through the dating apps or linger at a bar to catch some cute guy’s phone number?

I want to help you by preparing your heart and mind before you dive into the dating world. If you’re not ready, you’re going to feel like you’re diving straight into concrete.

I’m here to help you navigate technology and get comfortable with first dates. I want you to find someone who is worthy of your time and will appreciate you the way you deserve.

Preparing Your Heart and Mind

My first rule: make sure you mourn your last relationship. You need to reflect on it. Process the boogers out of it before seeing someone else; otherwise, you’ll be trying to process your breakup and meet someone at the same time, which will be messy. Your brain will be overstimulated; there is a risk that when you’re finally over the breakup… you’ll break things off with your new partner.

Sometimes it’s unavoidable to process the death of a relationship while also seeing someone. 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 a doozy to process. A marriage that long has a lot of history, and potentially children attached to it. Someone new will have to respect your past; otherwise, they may get the boot.

Before you put on the red dress and heels — or the nice suit and tie — you need to do a little bit of self-care. Your homework might entail the following:

  • Find a therapist or other professional to help you 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. I encourage you to process your grief, not bury it. A therapist or other professional can give you direction and much-needed 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. Throw those things in a fire, shred papers and pictures, and donate clothes to Goodwill.
  • Spend quiet time in meditation and/or journal 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; there are many swoonworthy characters, stunning clothes, and plotlines to distract you and give you hope for love. Romantic comedies are a good way to refresh the heart and help you figure out what you want. Watch Bridgerton just for the duke. He has a heck of a pretty face. You need lazy comfort days. You need to study the differences between healthy and toxic relationships.
  • 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 group hotlines and Internet forums.
  • 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 a while, 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.

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. We become insular and our social skills take a hit. When you are around more people this can help you to learn new communication methods.

When you get back into the swing of dating, take things slow. You don't need to prove anything.

When you get back into the swing of dating, take things slow. You don't need to prove anything.

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 was dating a man online, and everything seemed okay at first. Then the man realized she was recently divorced, so he asked her for her alimony to pay for his new laundromat. She dumped him.

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/she is hiding something. 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 ALL THE TIME. 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 to 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 the police or report the website to the BBB.

You need to be careful. Read up on dating sites before you join them. A lot of online dating is just hooking up. Businesses make money off your dating profile, and they don’t care whether you really get matched up with someone or not. They’d actually prefer you don’t successfully find someone, so you keep coming back to use their website and continue to pay for their services.

Enlist Your Friends

It can be overwhelming to piece together your dating profile. Having second eyes will ensure that you pick the right pictures, the right interests, and the right words to catch the right person’s attention.

Your friends will likely have good dating tips for you if they’ve been doing online dating for a while. 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. Couples often get set up by 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: 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 and get a general idea of their dating history.

Keep things simple. You don't have to impress your date with every detail about yourself. Leave a little mystery.

Keep things simple. You don't have to impress your date with every detail about yourself. Leave a little mystery.

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. 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 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 set up yourself so you attract luck.)

Where to Go

I recommend for a first date to meet up on an afternoon, particularly on a Saturday or Sunday. Look for charming things to do that might help break the ice: explore an orchard, visit a new place, go to a coffee shop, check out a downtown area you’ve never visited, stroll through a museum or botanical gardens, and maybe go to the 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 something 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 pink. 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 homeless.
  • Don’t wear loose or ill-fitting clothes.
  • Don’t wear clothes with tricky pieces or unreliable zippers and buttons.
  • Don’t load up on 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 or images.
  • 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, funny, and smart. 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 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 boring.
  • Ask about what they do in their free time and some of their favorite things about the city.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2020 Andrea Lawrence