A
female
age
41-50,
*ronco love
writes:Hi, I'm in my mid forties and have had a crush on a childhood boy/ man now, for years. We've never had a full conversation before besides saying "hi". From what I've observed, he seemed to be the quiet type when it comes to girls/ ladies. Our families have multiple connections and are very close. Side note: I recently lost 120 lbs so I look a little different than when I did as a child or my younger adult years.. Well, a lot different. Anyway, this fall, after the loss of my first 80 lbs, a close family friend and my crush's step mother passed away suddenly. So I traveled, locally, back to my hometown to pay my respects before the funeral. While visiting the family, I ran into my crush's mother. She mentioned that her son was in town for the funeral and invited me to come by the next day. Of course, I was smiling from ear to ear, but also wondered how she knew I had that crush on her son or was she just playing match maker.The next day, after the funeral, I ran into his mother at the repass. She immediately found her son and brought him over. He greeted me with a hug (the first one ever) and we all chatted in a group. It felt very awkward, I was enjoying every minute of it. We all then went our separate ways. A complete fail. I should have flirted or said something so that we could connect later, but I fumbled. A few months later, I opened up my Facebook and noticed a new friend request. It was from my crush. My first instinct was to immediately accept it and think later. I thought, Why did he friend request me now? We have/ had common fb friends before and we were even Facebook friends years and years ago in the early Facebook past. All these questions are coming in my head like: We are both 44 years old, does this friend request mean anything? Does he want to connect? Did he look for me on FB? Should I say something first? I just don't know what to do. We are getting old. He's single, and I'm single. Should I just bite the bullet and ask him out for coffee the next time he's in town? If so, how do I start the convo to even ask him? Or should I just leave it alone and wait for him to contact me? Please help...
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female
reader, Honeypie + ♥, writes (21 March 2021):
 Absolutely agree with the guys here, HOLD your horses.
You had a crush on this guy as a CHILD and have built him up to be this AMAZING man, that he may or may NOT be.
You have never had an actual conversation, you have no idea who he is and how his life has been.
Sure, ask him out for coffee but really try and rein in those romantic feelings of yours. If coffee goes well, maybe wait and see if HE will then ask you out. DO NOT do all the "chasing" it makes you seem desperate.
Take your time getting to know him.
And no, it would NOT have been appropriate to be all flirty at a funeral - where is your common sense, OP?!!
A
reader, anonymous, writes (21 March 2021): Please calm-down and assume the dignity of a sophisticated adult-female in her 40's! If you were 16, you'd be expected to fawn over someone you were crushing over in your high school class. You're adults, so grown-ups don't have to play "secret-admirer." We can invite each-other out for coffee, we can make dinner dates, and we can meet for lunch. With no strings attached or ulterior motives!
I'm asking you to calm-down, because I don't see enough enthusiasm from his corner to hit the gaga-button and shower everybody with confetti.
I'd take a chill-pill to compose myself; and then I'd send the gentlemen an IM via Facebook. Telling him how lovely it was to see him after so many years; but how you wished it could have been under more cheerful circumstances. His mother is a woman, women can usually see through each-other. It was obvious in the past you liked her son. She has known you since you were a girl; and probably noticed your gazes and behavior when he was around. He's apparently still single (a bachelor at 44?) I wouldn't be so quick to get your hopes up! Was he continuously single all these years? Has he ever been married or engaged? Did he recently breakup with someone? Could he be dating someone his mother is not aware of? Does he even like women?
Get your feelings and emotions grounded and under control; so you can deal with this on the clear-headed adult-level. Yes, you can make the first move; and suggest some kind of cordial meeting where you can get to know each-other. Catch-up on all the years gone-by. Feel-out his character, values, and personality. You might not like him at all!
You can even flirt, if you feel comfortable enough to...just don't be all over yourself, or too giddy! Show some confidence and poise. Don't exalt the guy to an elevated status before you even know who he is as a man, and what he stands for; after so many years since you were both children. Tribal politics and racial-tensions has brought-out the worst in people these days. Don't overlook poor-character or bigotry, or delude yourself.
You know of him, but you don't know his past, or his true personality. You've both lived full-lives; and you've been separated for too many years to be the same you were even in your 20's!
First and foremost, he has more to appreciate about you than your appearance. Personalities and character are just as important; even moreso, because that lasts far beyond our looks!
Don't set your expectations on a romance; because you don't know if he is looking for anything serious. You don't know if you're his type, which does not mean you're not good enough...it means you're not the personality-type compatible with his. That's all! If anything more than that, you won't know unless he specifically spells it out verbally for you. Leave as little to guessing as possible. Judge by what what you see with your eyes, and hear with your ears.
Go in open-minded, level-headed, and see if the crush is simply a young-girl's leftover fantasy-dreamboy; or if he measures-up to your expectations in reality. Proceed with reasonable caution. You don't really know him, but you're about to get more acquainted. You're familiar through past connections; but people change over the years. Just as you have.
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A
male
reader, kenny  + ♥, writes (21 March 2021):
 She probably never knew that you had a crush on her son, neither was she playing match maker. You are a close friend of the family as she was more than likely just being polite.
I would not really read to much into him friend requesting you on facebook, again he probably just remembered your recent encounter so thought it would be nice to add you on FB.
In this day and age its not uncommon for a women to make the first move on a guy, so why not bite the bullet as you say and just ask him out for coffee.
By asking if out for coffee you won't be losing face if he declines your offer, as you could just very well have been being friendly and wanting a catch up.
Contact him and ask him out for coffee and just see what happens, thats all you can do really.
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