Dear Shawna, I am a 35-year-old with no kids who has never been married. I am a Career driven female who has just landed her dream job. Although I have friends close by, I find myself choosing to spend a lot of time with a gentleman I recently met. He happens to be a lot older than me. We enjoy each other’s company, the conversation is phenomenal, and the physical connection is undeniably electrifying even though the age gap is about 19 years, give or take.
But, while on a recent dinner date with him, I learned his son and I went to the same College. We shared the same group of friends. We even “dated” casually. Do I tell him I know his son, or do I leave that part out? I don’t want to start a relationship being deceitful, but I also don’t want to lose a potentially great man because of a past College Fling, if you can even call it that. HELP!
Let me start by congratulating you on your dream job. Second of all, how do you feel about being a stepmom? Ha, Ha. Just Kidding. Kind of. I definitely wouldn’t let a “fling” of the past interfere with the possibility of a future with, let’s call him, Pops. After all, you said it was just a couple of dates between you all. So No, I don’t think you need to tell him anything.
We will refer to the son as Matt. If you and Matt have ever had a physical relationship of any kind, this becomes less than classy and boarder line classic Jerry Springer episode.
Unless, of course, you don’t remember ALL the details. If you don’t know, it didn’t happen.
I would have already done my research on Matt. The night you realized you knew him. If you need a burner account, I have one on all platforms; thank me later. Scratch that; I’m probably the best online private detective ever born. My investigation skills to find out all the details are top-notch and somewhat creepy. I’m better and more equipped for this kind of online snooping. So send me his name, and I’ll run a full report and get back to you in 2 hours. I’ll need an hour and 15 minutes for an iced coffee run.
But for future reference, I’ll share a little knowledge in a field I’m overqualified. You need to Find out If Matt is married. If he is married, the likelihood of him mentioning you all hanging out with his dad is slim to none. Okay, so He is married. He isn’t holding on to the hope of marrying you. Hate to break it to you, but your study buddy from College has moved on to greener pastures. But so have you. Pops has got to be a Vintage charmer if you are this involved so early on. I don’t know about you, but I’ve never known a remake to be better than the original. Just look at all of the remakes in movies. Nothing comes close to the original. Songs? Same thing, remakes are trash most of the time!
Also, research who Matt is married to. Make sure it’s not someone y’all both know. If you know her, Run. I know It is Halloween season, but I don’t think these are the skeletons you want coming out of the closet. If you don’t know her, all Systems are Go for the Catch a silver fox mission.
Not ready to be a stepmom or possibly even a Grandma? Have a well-thought-out excuse prepared to use if you are invited to any of the holiday events. Chances are if you aren’t being told about his holiday plans or asked to join him by the 2nd Monday in November. I think it’s safe to say your invitation to Family Palooza 2022 will not happen.
If you follow my lead and land yourself an invite, He considers you a “potential” asset in his personal life. Let me say you are well on your way to becoming the proud owner of a silver fox. Remember, dress to impress. You aren’t dating just anyone. You are dating Matt’s dad. Matt, the guy at one point in your sleep-deprived college days, thought was a match for you. So, no slits so high that the implosive, younger, carefree lifestyle you once lived show up and shows out in all its 2005 trendy Butterfly tattoo glory at the family thanksgiving lunch.
May I suggest a simple Hillary Clinton-style power suit? SIKE! Never, NEVER a full power suit. Every time I see a solid-colored women’s power suit, I cringe. It reminds me of the suits Hillary Clinton wore way back when. Oh man, those bad boys were appalling. She has one in every color. Bless her heart.
After you follow all these simple instructions, You will exude an energy that screams you are a beautiful fashionista whose vibrant personality and willingness to take chances in life will pay off, whether it’s as a potential future Mrs. or just a little younger date to cause a stir at the Family Thanksgiving 2022.
Ps. I emailed you the address I want my upcoming wedding invites sent. No way you can walk away single after all the knowledge I shared. It will either help you find your forever or find all the red flags needed to tuck tail and run.
~ Shawna~