12 Roses of the Winning Gentleman

Written By Andrea Cladis

Author Bio: Andrea is the author of Finding the Finish Line: Navigating the Race of Life through Faith and Fitness (CrossLink, 2017). She is Summa Cum Laude graduate of Elmhurst College with degrees in English Writing, Communications, and French. She has worked for Delnor Hospital’s Marketing and PR Department, for neighborhood magazines, and as a feature writer for Shaw Suburban Media. Andrea is currently working on an MFA in Writing at Fairfield University and works as a High School English Teacher, Group Fitness Instructor, and freelance writing consultant. When she’s not writing or dancing, you can find her baking, reading, competing in Triathlons or Marathons, spending time with family, or serving at her local church. Known for her opinion columns, Andrea’s writing has been described as “emotive, yet brazen, seasoned with thinly veiled cynicism, and a pinch of sarcasm.” - Website: andreacladis.com - Facebook: @WriterAndi - Twitter: @AndiCladis


The ultimate to-do list for the man looking to win the woman worthy of his heart and for the woman looking to find the man who deserves hers.

Chasing a woman is a full time job. Honestly. Truthfully. As the overused cliché goes, any woman worth chasing won’t be easy, but she’ll be worth it. Likewise, any man worth loving deserves to be treated with the utmost dignity and respect.

After the surprise of receiving twelve gorgeous long-stemmed roses on a first date with an ever-impressive young man whom I dated for over a year, I created this to-do list of the twelve most notable, non-negotiable behaviors, attitudes, and insights exhibited by the type of consummate gentleman who is absolutely worth waiting for.

Rose 1: Demonstrate initial interest through actions. Be on time. Create a memorable first date. Be spontaneous, inquisitive, and attentive. 

On a cold and snowy February morning, dressed in a cozy, new, knitted maroon poncho sweater, slim black leggings and knee high boots, I meandered around the corner of a neighborhood coffee shop pretending to be interested in the rustic coffee mugs for sale. Hair curled flawlessly and make-up carefully done, I awaited the arrival of the man I was supposed to meet that morning. I looked outside as a gentle snow delicately manicured the town and the worn coffee shop presented itself as an inviting place for casual, comfortable conversation. Cautious as I’d always been in meeting new people, especially those met through online forums, I chose a first meeting place on home turf. I was familiar with the coffee shop and I supposed if he ended up being some psycho, I was confident the people who frequent the venue would ensure my safety. Also, the mindset I held was if a man really wanted to meet me, he’d be willing to make a drive my way. If not, I’d know right away he wasn’t all that serious. Simple, but not manipulative, this is a preferred strategy of mine to ensure that the initial interest on the man’s end is high.

Checking my phone for progress updates on his travels, I anxiously anticipated meeting the Greek man who had garnered my interest from the beginning. Attractive, successful, intelligent, family-oriented, and kind. Oh, and Greek! After all, dating a man from a Greek family was once a mandatory part of my early foray into dating. I was nervously standing there, waiting, repeating his name, and excitedly thinking what all women of a certain age confound themselves with on a regular basis: Could he be the one? Will he be? Is this it?

Rose #2: Establish genuine trust. And bring flowers! Or plan a gesture of surprise.

Greeks are notoriously late, so knowing this I didn’t hold that against him and he had been in contact with me regarding his travel time, so I was content. So far, so good!

I can recollect other first dates when I met someone who arrived long before our scheduled time and seemed bored by the time I arrived, which made the date unnecessarily awkward, or those men who casually arrived late thinking a late arrival elevated the cool factor of their stride as they’d stroll into the meeting place. Hint: Coming late with arrogant swagger? Instant turn off.

Instant turn on? Walking in not more than a few minutes late, hair well-styled, wearing a dark leather jacket, crisp jeans, and cradling an armful of 12 long-stemmed roses and making eye contact with ease. Seriously? There he was. Wow. Never before had I ever been given flowers on a first date or let alone a tenth date or not to mention, long-stemmed roses! Classy, elegant, not too flirty, and a favorable way to make a strong first impression. Greeting me with a smile, firm handshake, and perhaps the most stunningly vibrant red roses I have ever seen in my life – and yes, I mean this, Alexander had me nervously adjusting my hair, grasping for lip gloss in my purse and wanting to step up my own first impression game! Feeling badly I didn’t have anything for him, he asked to take my coat and we found a place to sit together. Pulling out my chair he entered conversation with a certain sense of reserve and acknowledgement. He didn’t feed me a line about how I beautiful I looked or what the weather was like; he simply thanked me for meeting him and offered to get us something to drink and eat. Not too forward, but still confident, I felt my heart beating faster in my chest and that underarm sweat was rapidly making itself known.

Rose 3: Gently initiate calming leadership. Do the little things for her that matter most. 

Noticing I was nervous, he placed the roses by my purse so they would not be of distraction on the table and I slowly felt my confidence coming back. I asked him several questions and our conversation was upbeat, engaging, and natural. He showed genuine interest in my life and was encouraging of the things that I cared about. We laughed, smiled, and enjoyed discourse until the early hours of the afternoon.

Rose 4: Make her safety your top priority.

After we had determined a time and location for a second date, I eagerly embraced my roses and he assisted me with my jacket and walked me to my car. The snow had accumulated greatly during our time together and my car was covered with snow and ice. Acting upon this situation without request, Alexander immediately ran to his car, which was over a block away, and quickly returned with a brush, shovel, and tool to melt ice. Allowing me to sit down and warm up inside of my car, I watched as he meticulously cleared my car of snow while he shivered in the wind. I felt more than cared for in that moment. 

I thanked him for his kindness and he made sure that I got off safely and even doubled checked to make sure I made it home since the snowstorm was significant that evening.

Rose 5: Give her countless reasons to feel worthy.

When I arrived home and pulled into the garage I sat in my car astounded not just by my clean and de-iced windshield, but by the roses sitting in the seat next to me, the smile still on my face, and the way I felt so worthy and cared for, all in the span of a few hours. 

Rose 6: Take her out! But respect her preferences.

A few dates later Alexander invited me out to a fancy dessert bar during the Lenten season. Not expecting that the venue would only serve wine and chocolate, I was somewhat at a loss when I arrived. Certainly, wine and chocolate would have been a perfect date, as I love both. However, I had given up chocolate for Lent! When Alexander realized this, he felt terribly that he did not know and he was adamant that would have selected another venue. Most importantly, though, he respected my decision to not indulge in chocolate that evening as we both shared and had vigilant intentions with Greek Orthodox faith and traditions. 

Rose 7: Do the unexpected, unrequired things to show how much you care.

Perhaps the best result of this entire scenario, however, was the week after Lent when he drove out my way to meet for a long spring walk in the park and he arrived with a cooler in his car full of expensive, upscale, artistically enticing chocolates and a bottle of my favorite wine. Not to mention, he gave me a card with a personal note and a Greek phrase I adored inside. He was ever the gentleman and I never felt less than worthy in his presence. 

Rose 8: Show your support! Make her signs. Make her something to eat. Be a man. That means you should eat, too! Even if it’s a weird vegan dish!

A month later he made signs for a triathlon I competed in and followed me along the course cheering me on the entire time! Afterwards, he cooked me an incredible vegan post-race meal. Even though I’m convinced his Yia-Yia assisted with the prep, I was impressed and it was absolutely exquisite.

Rose 9: Be gentle, but challenge her when she needs it. Listen to her. Love her the way she needs to be loved, not the way you expect to be loved.

Alexander was a different type of man. A worthy, genuine gentleman. He must have been raised right, likely by no-nonsense Greek grandmother’s yielding metal hangers, and I felt lucky to be cared for and loved and to have had the experiences we did. Even now when I look back on our time together, I am fulfilled in the sense of the gratification and joy it brought to my life. Over the course of our relationship, he remained consistent in his actions and I never once stopped to question my value or worth not just to him, but in who I am as a person.

Rose 10: Take pride in who you are and let her support you in that. By all means, let her love you!

Alexander was proud of who he was, but he was not an arrogant man in any way. He exuded humility in all things and did not degrade those around him. He celebrated his successes and he worked harder in his failures. He was easy to love because he loved himself as a man of character, of God, and of worth and purpose. And in respect to us? “The chase” wasn’t one of honing a definitive outcome, but rather it was one of respect and dignified pursuit. It created comfort and contentment. It produced love; it didn’t tear it down. And for the reason, I loved every part of it.

Rose 11: Don’t make broad generalizations about all women or assumptions about her actions based on her sex as a woman. Hold her to high standards, but give her a chance to stand apart and treat her differently from day one. 

I would give anything to be in that moment again with long-stemmed roses in hand, wondering in awe what I had done to deserve such a thoughtful gesture. 

He did everything right even though we didn’t work out. The romantic chemistry never really found a steady foothold between us, but we didn’t part ways with any degree of animosity, only for sadness of lost friendship. 

Yet the man who brought me roses, bought me coffee and chocolates, listened, smiled kindly in interest, and willingly buried himself in snow on my behalf is not someone who will be forgotten. He was a man of inherent worth, who made me, a relatively unassuming woman, feel like a woman of honor. 

Rose 12: Don’t hurt her. Whether a first date, a last date, or a forever date, do your best not to hurt her emotionally. She’s fragile. She’s been broken before and even though she’s strong enough to shrug it off, don’t let her get to the point where she’d rather shrug you off. Be that rock for her. Don’t belittle and don’t mock. She deserves the best. Be the one to give it to her. If you show her you can be that man she’ll never again have the need to close her heart. 

Gentlemen do exist and they’re worth waiting for. Women can be won and they are worth fighting for. These men might not be Greek Gods bearing roses and shoveling snow and the women may not be PMS-free goddesses either, but the moment you feel respected and cared for by someone who continually gives eagerly, selflessly, and with an authenticity of compassion, you might want to ease up on the chase because it may finally be time to let yourself get caught.