Why You Shouldn’t Be Afraid to Date a Younger Man

Happy New Year! And what better way to start the new year than with a spring and summer romance. Winning the lottery wouldn’t have hurt, but this is a close second.

Yep, I’ve joined the ranks of Demi, Cher and Vivica A. Fox. I’m seeing a young man. NO ONE would have believed this. Mainly me.

My arguement for not accepting numerous dates I’ve been asked on by younger suitor was, “I’m not trying to raise no half grown ass man!” I didn’t think men my age possessed the maturity I require in a relationship. I was not about to enter into something with someone who I know is of the XBox generation – – sitting around playing hours of video games, drinking crunk juice and listening to Ludacris was not on my agenda of things to do. What changed my mind? Winning a 25 year old in a contest. Here’s how it happened.

With my family being displaced by Hurricane Katrina I had been assisting them with resources to help rebuild their lives. In the process of helping, many people reached out to me to assist ME in my efforts. One of those people was Comic View and Def Jam comedian Hope Flood. This wonderful lady decided to take me and a few other women out for a special day of rest and relaxation (she calls it A Day of Hope). After that day of pampering I thought we would all say our good-bye’s and go back to being just “us”. But, Hope, being the fantastic person she is maintained contact with us all. She would check in to see how my family was doing and to ask if she could offer any more help.

One day Hope contacted me to invite me and some of the other ladies to her comedy show as special guest. This comedy show takes place at Club Atlantis in Dallas, TX. As always, I was going to try and finagle my way out of it. I really do not like clubs and was not feeling it. But, for all that Hope has done for this community and my family, I was willing to go to support the cause.

It wasn’t just a comedy show, it was a Jazz session, jokes and various contests – hence the show being called “Jokes & Jazz”. I had a great time. One beer and a apple martini later had me looser than a slinky.

One of the contest Hope devised came with a reward of two tickets to the play “Why do Good Girls like Bad Boys”. I had heard about this play and really wanted to go see it. Unfortunetly a financial snafu (I was broke) was preventing me from attending. All the contestant had to do was sing the theme song for the Jeffersons. Well, I love a challenge and due to my incrediable vocal range, I knew I’d win this contest hands down – – plus, I was the only one to enter!

I gave a stellar performance that ended with a standing ovation . . . They may have been applauding or leaving. I’m not really sure, but I won the tickets.

After getting my gift I started going through my mental rolodex of who I wanted to take to this play. I really didn’t want to take any of my girls. No disrespect to them but single and potentially angry women seeing a play about men acting up could produce some negative conversation about “triflin ass men” I’m trying to avoid in the new year. I could have taken a male friend, but the only one I have would have talked through most of the play and I didn’t feel like choking him. Then I realized, this was a moment to seize an opportunity I would not have normally taken. I turned to Patti (one of my Day of Hope buddies) and said, “I need a date!” Patti of course looked at me as if I had drank a bucket of martini’s. “I need to ask Hope to get me a date!”, I reiterated.

Patti dashed over to Hope to ask if she could get me a date. After Patti returned to our table I was a bit apprehensive about what I had requested. But, the deed had been done and I was not about to ask this 5 foot tall sistah who will cuss out a grown man to forget what I had said. The dye had been cast and I was about to ge the hook-up “Hope” style.

Hope came to the stage and asked all of the single men to raise their hands. About 7 hands went up. She informed them that I needed a date for the play and for those who were truly single to come to the stage. 5 guys came forward.

Guy #1 was immediately eliminated because Hope knew him personally. Apparently the level of triffling he possessed was too toxic for even one evening out.

Guy #2 was eliminated because he was a Piseces. I’m not indeptly familiar with astrology, but I don’t think the fish people and the Leo’s get along well.

Guy #3 was eliminated for professing to be a “Parking Lot Pimp”. . . . I was stumped someone would admit to something like that. For those of you who have no knowledge of the Parking Lot Pimp occupation – – It’s the brother who waits outside of the club to pick women up in the parking lot because he’s too cheap to pay the cover charge. . . . Yes – triffling personafied.

We were now down to two men. They were both asked the basic first date questions:

– Are you married?
– Are you divorced?
– When was your divorce final?
– Did a judge sign a decree of dissolutionment?
– How many kids do you have – – you know about?
– Do you have warrants?!!!
– Are you on medication (mood altering drugs or anything for STD’s)?

The last question was “How would you make Gail feel special and respected?” I can’t remember what either one of them said, but I figured it was BS and dismissed it anyway.
Since both of them were cute, I asked the audience to make the final decision for me. Before I took the audiences advice I asked Hope to ask them how old they were becasue they both looked young and I didn’t want to go out with anyone in their 20’s. I just didn’t want to deal with some immature joker with no life experience who may have been looking for a sugar mama.
Hope advised me on the maturity levels of men. Her exact words were, “Gail, there are 50 year old M*%^$#F*&^%$’s with issues! Age don’t matter!” It’s that bold, no holds bar response that made me shut up and accept the audience’s choice.
We took the vote by applause. The winner was . . . cute to say the least. He appeared to be . . . maybe 27. He also was at the club with about 30 of his closest friends and they out clapped and out yelled everyone in the club guaranteeing him a win.
I took a deep breath, went back to the table and exchanged contact information with him. My paranoid nature with men almost caused me to give him a bogus number. But, something he did made me want to, at the least, get to know him. He put his hand on my waist and moved me out of the way of the drunk folks. I thought it was such a gallant move. Plus, he had a soft touch.

The day of the play I was actually going to stand him up. No, I’m not a mean spirited woman. I’m a 40 year old woman who didn’t want to go out with a child! But after talking with ALL of my girlfriends and sisters, I decided to act like Nike and “Just do it.” Some of my girlfriends have son’s in their 20’s. One said, “If he’s mature enough, go for it. You can come and get this lazy bastard but then that would end our friendship.” Needless to say, all of my friends were supportive.

It was just a date . . . Something I hadn’t had since Clinton was in office. I was not going to let this young man’s age stop me from an evening out.

We stayed in touch that week and made plans to meet for the play. We decided to do everything dutch and to meet there since we both live 20 miles from the meeting place – in opposite directions.

My natural defensive nature prompted me to tell him, “If you’re looking for a sugar mama you’re out of luck because I’m broke!” He gently told me his funds were tied up in his daughters college fund and making sure his land was cared for. . . . . Daughter? Land? Baby boy was already five steps ahead of most 40 year old men I’ve met and 8 ahead of me. A child . . . land . . . could he actually be a responsible adult?!

We met for the play on a cold, rainy Sunday afternoon. Our conversation was easy. It was like we sort of knew each other. Since I had no expectations I allowed myself to just chill and have a good time. We talked prior to the play starting. We shared our thoughts on perfume (the lady in front of us was toxic); scantly clad women (coohie cutters and cold weather are just a fashion DON’T); and who the heck were th people performing in this play.

During the play he brushed against my hands and realized they were very cold. My hands are always cold. Without prompting, he took my hands into his and started to warm them up. He wasn’t being fresh or freaky, just concerned. During intermission is when we talked about the play and then got to the question of age . “Okay”, I said. “How old are you?”

“What do you think?”, he replied.

“I’ll give you 27”, praying he was just a really young looking 35.

He smiled. “25”.

I stopped breathing for about 20 seconds. I have a nephew who is 27, married, with 4 children. Being on a date with someone younger than any of my nephews or nieces made me feel queasy. But, I had to realize I have sisters and brothers who are 10 to 14 years older than me.

After a few seconds he asked, “And you?” I couldn’t even say it. I just held up 4 fingers. I’m 9 years younger than his mother!!!!!!!!!!!

We went to get something to eat after the play. At first I thought he was trying to lose me in traffic, driving like he was auditioning to be in the Indy 500. Once we got to the resturant he told me he wanted to see if I could keep up. He’s funny.
During our conversation I realized this man-child had more life experience than me; having experienced the lost of a child, growing up and graduating from the school of hard knocks and over coming many small town adversities. Many of our experiences were similar: he’s an Iraqi veteran, I’m a desert storm vet; both of us have traveled the world; we both have a knack for networking; and we both want to make positive differences to up coming generations. We also are both very adventuous, frugal and have an affinity to martini’s. All of that and he seems to be quite balanced.

He is 25. I recall being 25. Living life with reckless abandond with an untainted spirit; willing to try anything new and deal with the consequences later. He has the XBox, listens to the latest rap music and goes to clubs on the weekend. He has challenged me to a video game, invited me to swing dance and helps me to understand the latest rap music. He does not alter his persona to match mine, nor do I attempt to step into his chronology. He is 25 and I am 40. Meaning, we need to celebrate the similarities and learn from the differences. I do not want, for a second, to be 25 again. He needs to pace his trek to 40. Although 25, mature and responsible, he should live his life like someone 25. Making the mistakes of his generation, learning from them and setting an example for those coming behind him. But, I hope he retains that . . . innocence . . . that zest for life we tend to lose along the way. The desire to hold a woman’s hand in public; not caring what his friends think. For him to remember that chivarly will win a woman’s heart quicker than a shiny truck or deep pockets. For him to continue to want to change the world for the better and not give up based on someone else’s judgement of him. For him to continue to have a song in his heart and be willing to sing it willingly to soothe my hectic day.

Now, I bet you’re wondering . . . will this be a romance to shame Demi and Ashton. Well . . . no! He is a career military man and will be shipping to his next base within weeks. We decided on the first date to play it by ear. Once he got his orders we bonded as friends. Plus, I’m not trying to be sitting here in Texas singing sad love songs while he sees the rest of the world. The current Mariah Carey compulation would work best during a break-up. But, it ain’t happening.

I’m glad I let my defences down and allowed this man to step into my life. Our friendship has helped me to let down some of my barriers. Yep, I got man issues. I do not like being disrespected or played. Being with someone who has been raised right and hasn’t bought into the game has given me hope that their are others out there. Understanding that building friendships is just as (if not more) important than having romance.

So, to all of my single, over 40 sister’s . . . when you’re asked out by a young man just keep Hope’s statement in mind: “There are 50 year old M*&%^&F*&^@#$’s with issues.” Plus, if he’s in the military and old enough and willing to die for his country . . . consider it your civic duty to at least go to lunch with him!

Now, here are some things you should keep in mind if you’re going to step out of your box:

Be honest with yourself.

If you are ready to get married and are specifically looking for a life long mate – – you may want to stay away from the 20 year olds. Remember your 20’s and left them live their lives. Now, there are some exceptions. I know of several young men who want to get married and start families right away. They feel that women their age are playing games and they want to by-pass all of that. They may be good candidates for women who are ready, willing and able to marry and conceive within a short period of time.

Pray he loves an extensive genre of music.

I would die a slow death if I had to listen to hours of today’s rap music. I don’t care whose having sex with whom in the back seat of the Escalade. For the love of Pete!!!! are people really having that much sex?!!!! I’m still, slightly stuck in the “good girl” vortex. These songs now a days have me wanting to smoke a cigarette and repent all at the same time. Confusion I tell you!

Who has more to lose

Don’t think because you’re older that you have more to lose in a relationship with a younger man. My young friend has land! I have a mortgage. He has a child. I have plants. Who do you think would be or should be more guarded?

Don’t assume he will want more children

If you’re dealing with baby lust then you better ask many questions. I know many men my age who had their kids in their 20’s and were done. Now, I know just as many who had kids in their 20’s and are starting all over again at 40. Most twenty-something men I know who have kids are not trying to have anymore. NONE. Several have gone as far as to have gotten vasectomies. Communication means hearing what is said, not hearing what you want.

Don’t think you’re going to change or mold him

I personally can’t stand a punk ass man at any age. With me, you have to be you 24/7, 365. The only time I want to change someone is if they are in diapers, because that’s the only time it makes sense.

Our 20 and today’s 20 is very different. They really are go getters. They are buying land, luxury vehicle’s, have taken financial seminars and have a life plan. Now, that’s not all of them. Some are still living at home with their parents and are making babies and not claiming them. Those are the one’s we are avoiding. But, the others are a force to be reckoned.

Communication is the key.

Get some B-12 and Bee Pollen

These jokers have the energy level of a TWENTY year old. Be ready to do some stuff. It may be something as simple as going out dancing or watching games all weekend, eating spicy wings and drinking beer. At 40 all of that can be a challenge. Especially if you’ve had a structured job and are normally in bed by 10 PM. Not to mention missing a gall bladder and dealing with acid reflux!

Be real

As with any relationship, no one wants to see the real you 2 years after the fact. If you’re fat with a lazy eye and have a bad fashion sense and he still hangs with you; count it all joy and have fun. You know you will read a man whose your age the riot act if he says something about your weave, gray contacts and silicon boobs. If you have attached parts, trust me, a young man is going to have questions unless you’re just a booty call.

Most important

Have fun. Life is too short to sit idle while watching it go by.

By hanging with my new friend I have realized how stagnant my life has become. I have been so busy being grown, I forgot how to live life and have fun.

If you’re dating anyone you should be having a great time getting to know lthat person. But should he be younger than you . . . just realize; age may be nothing but a number, but maturity is a state of mind. If he’smature enough . . . enjoy getting to know a new friend.

Lastly, if you’re in the Dallas area and plan to stop into Club Atlantis on a Thursday for Jokes and Jazz, study your pop culture the night before. Hope ain’t no joke and will challenge you for those tickets.

Ciao!