When it comes to dating successfully, the cards may seem they are often stacked against you. There are so many things to consider these days. Do you swipe left or right? If you swiped left when you meant to swipe right, can you fix it or is that person gone forever? If you swiped right when you should have swiped left, what do you do if it’s a match and you have no interest? Should you pay for an upgraded profile, or are you wasting your money? Do you really have to answer every single message you receive? All of these questions – or more – and you haven’t even had your first conversation. And what IF that attractive stranger, who could possibly be a scammer, might also be a troll just looking for a hookup?

If dating feels more like browsing the “Wanted” posters at the local post office than finding a true connection with someone you’d like to spend time with, know you’re not alone. Those of us out here braving the endless supply of dating apps, with the honest intention of finding someone to love, are often experiencing the same.

Let’s examine some real-life dating situations, then ask a couple of dating and relationship coaches their advice. Joanna Shakti is the Founder of Ecstatic Intimacy
at www.ecstaticintimacy.com and Matthew Hale, M.A., IMFT is a Couples Counselor, Relationship Coach, Individual Therapist, and Life Coach at www.growingself.com.

Photo: depositphotos

The Good

Kelly from Parker shares her story: “Will and I met on OK Cupid on Valentine’s Day in 2020. Things had gone a little crazy with the emergence of the coronavirus, but the reality of what was about to happen had not yet sunk in. We sent a few messages back and forth on the app, joking about spending Valentine’s Day on a dating site, then exchanged numbers so we could talk on the phone.

We took it slowly over the next two or three weeks, getting to know each other through text messages and phone calls, eventually wondering if we would ever meet in person as the world began to shut down around us. Then one day, Will asked me to meet him for lunch. Restaurants had started to open up for take-out and it was a beautiful, sunny, spring day. We decided to meet at the restaurant, order our food, then find a place to eat outside where we could finally spend time with each other in person.

When I arrived at the restaurant, Will met me in the parking lot. I laughed when, instead of flowers, he handed me a small bag filled with face masks, hand sanitizer, and gloves. He opened his trunk and pulled out two brand new camping chairs which he set up behind his car. We talked and laughed and pretended for the moment that everything was normal. I smiled as I realized how perfect it was that Will had thought of everything, down to the last detail. That pandemic picnic in the parking lot was one of the best dates I’ve ever had.”

JS: “Details make the difference. Feel into the right timing. Choose the right place for the two of you. Every connection is different. Create experiences, even at the beginning, that are aligned for both of you. It might sound like more work, but that care and attention, even for a ‘coffee’ date, matters in seeing if a connection is real. Real for the long term.”

MH: “Will did an excellent job planning for a date with lots of obstacles in the way. He was adaptive and creative, which provides a memorable dating experience. One thing that needs to be highlighted is that the first date did not cost very much money, and that is perfect. There are so many first date ideas that cost zero dollars and still fulfill the purpose of getting to know someone on a more intimate level while having fun. This is important information for people planning the date, and also for those who might have high expectations for a first date. Do not let the amount of money spent on a date become an indicator of someone’s romantic interests.”

“One thing that needs to be highlighted is that the first date did not cost very much money, and that is perfect.”

Photo: depositphotos

The Bad

Ann from Thornton recounts this experience: “After spending the afternoon together on our first date, Jason asked me if I wanted to stop for an early dinner before he took me home. At the restaurant, as we were seated at our table, the server handed us our menus and pointed out the table tent that listed the happy hour specials with ½ priced beers and $5 appetizers. Before I could look at the menu, Jason ordered two beers and two appetizers, then told the server that would be all we were having. I was a little surprised that he hadn’t asked me what I liked before taking complete control of my order, but rather than make a scene, I just let it go.

When the server arrived with our beers and appetizers, she set the plates on the table. Jason reached into his mouth and from somewhere deep in the cavern of his mouth, fished out the biggest wad of gum I have ever seen and stuck it to the side of one of the appetizer plates, then he pushed the plate toward me and said, ‘Help yourself.’ I told him I wasn’t hungry, quickly finished my beer, and asked him to take me home. Of course, he made sure to retrieve his gum from the side of the plate and stick it back in his mouth before we left. A couple of days later, he had the nerve to ask me out on a second date. I declined.”

JS: “It’s true some people can be attracted to and turned on by assertive energy and someone that takes the lead. However, to be attractive, the assertive person must consider the needs, desires, and preferences of the other person. Assertiveness can be hot, being disrespectful is not.”

MH: “As a rule, first dates should be fun, easy, and brief, the idea is to leave them wanting more. On first dates you are trying your best to be charming, interesting, and funny; qualities that are not easy to maintain for long periods of time. After a while it becomes challenging to postpone ‘long term committed relationship behavior’ like leaving chewing gum on a plate. I notice one participant of this date not having a voice. I do not think it would ‘make a scene’ to simply state they were interested in something different and would like some more time to decide. It is good to know the difference between assertiveness and aggression. First dates should be enjoyable for each person, if there is something you are not enjoying, or something else you would rather do, speak up! It will allow your potential match to get to know your preferences and personality.”

“Assertiveness can be hot, being disrespectful is not.”

Photo: depositphotos

The Ugly

Cheryl from Wheat Ridge tells us about this uncomfortable date: “Steve and I exchanged a few quick messages on Bumble, then agreed to meet up for a drink or two on a patio. When I arrived, I immediately felt that there were no sparks, but that happens once in a while in online dating. No big deal. So we’d have a drink, make a little small talk, and move on with our lives. How bad could it be?

We ordered our drinks and, while we waited for them to arrive, I excused myself to use the restroom. I was only gone for a few short minutes. When I returned to the table, I noticed the drinks had arrived, Steve’s drink was already empty, and he was signing the tab. A little confused, I sat down and took a sip from my drink as he looked up and said, ‘This just isn’t going to work. I’ve paid the tab, so drink your drink and let’s go.’

Instantly, I felt the tears of embarrassment as they sprang to my eyes, but I quickly blinked them away. I took a breath, gained my composure, and said, ‘While you may be finished with your drink, I’m not finished with mine. I’m going to sit here as long as I like and enjoy this beautiful day. You can go.’

He continued to offer to stay until I was finished. I continued to hold back the tears as I insisted that he go. He finally left me to finish my drink in peace.”

JS: “Kindness counts. Rejection is inevitable in dating. It’s never comfortable, yet when we treat each other consciously, when we know the lack of chemistry isn’t personal, we can walk away with grace and our heads held high.The more comfortable you are in your own skin, the less someone else’s preferences can impact you and the more open you can stay for someone who is your match.”

MH: “I would recommend some more ‘getting to know you’ happening before meeting up. A few messages exchanged on Bumble before a date would not provide adequate information about this person and could also indicate that the intentions of the meetup are not for a potential relationship, but more of a hookup. Unfortunately there are some dates that will not go well, especially if you do not know some basic intentions of the other person. A good strategy for scenarios like this is to have an exit strategy. It is nice to let a reliable source know where you are going, and if you are nervous about the date, or if it goes sideways, you can use them as a reason to leave or have them come and get you.”

Photo: depositphotos

Dating Apps: The Good and The Bad

Hinge

Good: See who likes you for free so there’s no need to blindly swipe hoping for a match.
Bad: Have to pay to upgrade to set most dating preferences.

Bumble

Good: Empowers women to make the first move
Bad: Easy to miss a match forever if you don’t check the app every day

OKCupid

Good: The multitude of questions that range from playful to political to personal help get the conversation started
Bad: The match percentage may give a skewed impression of actual compatibility

Tinder

Good: Easy to use and wildly popular
Bad: Has a reputation of being “all about the hookups” which can lead to it being all about the hookups

Plenty of Fish

Good: Most features are free including messaging and advanced search
Bad: Sometimes you get what you pay for

Zoosk

Good: Uses Behavioral Matchmaking with verified profiles to increase the odds of meeting someone looking for the same thing
Bad: Most features, including messaging, require payment and it can quickly get expensive

eHarmony

Good: Has a long and successful track record of matching people who are looking for marriage with their well-known compatibility quiz
Bad: There is very little you can do for free so it requires a hefty financial commitment right from the start with no real option to try it out first

Match

Good: Brings people together from all over the globe expanding dating options while offering a matching algorithm to help narrow the choices
Bad: The upgraded version is required to contact other users and it can be a little on the pricey side.

Photo: depositphotos

The Do’s & Don’ts of Dating in the Digital Age

Do:

1. Follow the “Golden Rule.” Treat others as you would like to be treated.
2. Step outside your comfort zone. We all have a type, but let’s face it, how well has that worked out so far?
3. Be creative and have fun. Think outside the box. Laugh. Find the positive in the small details.
4. Spend some time on the phone before meeting in person. Prequalify your prospective dates. Are they looking for the same thing? Do they have the same values?
5. Lower your expectations, but raise your standards. The biggest misconception is that if you swipe long enough, the perfect person will magically appear. And when that doesn’t happen, you might be tempted to settle for less than what you deserve.
6. Date intentionally. Know what you want and don’t be afraid to ask for it.
7. Speak your truth. Be open, honest and transparent.

Don’t:

1. Be so picky. Perfection doesn’t exist. It’s okay to have a few dealbreakers, but relax a little on the other stuff.
2. Treat dating like a job interview or catalog shopping. Remember, dating is not a business transaction.
3. Overshare. It’s not necessary to share your whole life story on the first date. There will be time for that in the future.
4. Ignore the red flags. When your gut instinct tells you something isn’t right, trust it.
5. Cast yourself in the role of victim. When you portray yourself as a perpetual victim that needs to be rescued, it’s difficult to find someone who will treat you as an equal.
6. Use a lack of chemistry as an excuse to be rude. Once you have developed a connection, be upfront and honest if you’re not interested. Ghosting people is immature and hurtful.
7. Follow “The Rules.” Don’t play hard to get. Return texts and phone calls. Let the other person know you are interested. The right person will appreciate the effort.

The experiences shared here, as well as the advice suggested by the coaches, offer a good perspective on some of the important things to remember when dating. It’s not easy to balance the very real need for caution and safety when meeting a stranger for the first time with the openness and vulnerability required to find a genuine connection.

“Take your time getting to know each other. Plan your dates with creativity and resourcefulness. Have a sense of humor.”

It’s always important to take the other person’s feelings into consideration. Everyone has different needs and wants, so communication is key to success in dating. No matter how confident you are, dating can leave you open to feelings of rejection, unworthiness, and ugliness. Make sure to check in regularly with the people in your life who know and love you and can remind you that you deserve to be treated with courtesy and respect.

Joanna Shakti leaves us with one final thought that no matter how hopeless being single in the suburbs might feel, there is still hope. It just takes a little courage and a lot of honesty, with yourself and others: “Online dating can have an assembly line feel to it, but if you’re looking for a soulful connection, the one size fits all approach to dating won’t work. To find and experience a real depth of connection and chemistry, you have to be yourself – genuine, authentic – from the beginning. Honestly share what you’re looking for long term, from the start. Share your dreams and your deal breakers. Be real. Be honest. Be vulnerable. And, genuine love may find its way to you much sooner than you imagined.”