I was talking to a “male friend” of 20 years today. I’ll give you the back story upfront. We met in summer school in Brooklyn between my Junior and senior year of high school. Things didn’t work out between us because after six months of dating (mostly just walking to the bus stop together after school and talking on the phone) and no sex, he gave me an ultimatum. “You either come to my house on Monday so we could do it, or it’s over.” Even then, I didn’t take orders from men too well. With those words, it was over. We’ve remained in contact for the much of the past two decades although after our break-up, we never hooked up. Not once.

Back to today. He called me while I was on my lunch break. I was happy to hear from him – especially because I needed a male perspective on a situation I’m having with another guy. Naturally, after I told him my mini-crisis, he turned the subject to my relationship status. You STILL single?? Hold up. Are you sending me pictures of you or somebody else?? Cuz if that’s YOU, I don’t understand HOW you could still be single after ALL this time.” I replied jokingly, “I know right. I’m superimposing my face on other people’s bodies. [LOL]” He got a bit more serious with the conversation and went on to imply that something must be WRONG on my end if I’m still single after a year and a half. “That’s a LOOONG time,” he said. “If it’s been a year and a half and you still single, you must be doing something wrong.” Apparently, subconsciously I don’t WANT to be in a relationship, so I’m turning men away for the wrong reasons. I must be listening to keywords they say on the first date and judging them too prematurely – or expecting them to be on my level in some ways that are not necessary. He said I’m acting all young and vibrant, but I want an older man – and older men don’t act that way.

Dating a Younger Man: Is It Worth It?

So I gave him the rundown on a few men I’ve gone out with this year. One was 27 years old and has only been in the country for a year. I met him at a wedding. I caught the bouquet; he caught the garter. He has two small children (ages 3 and 4) back home in Jamaica and he’s bringing them to America as soon as he can. He was eager to get serious with me and talk about a potential future together after only one date. (huh?). Aside from that, he wore white, tight high-water pants and a velvet blazer on our first date. As soon as I pulled up to his house and saw him coming down the steps, I knew we wouldn’t make it. I get that I’m the “older woman” in this scenario, but just – no.

Next guy is 49 years old. Met him in the parking of a Trader Joes supermarket in New Jersey. He offered to help me with my bags and I graciously declined, but did accept his business card. (He refused to take my number but wanted me to take his. I called a few days later.) Great career – art director for a major television station, lovely Tudor-style home with a large backyard, nice car, perfect gentleman during the few times we went out (blah, blah, blah). Boring and passive. And he never called. Texted me 99% of the time, but seemed very excited the two times I took the initiative to call him. How do two mature people build a progressive friendship – and potential relationship, via text message? My take was that he expected me to take the lead and initiate something further. If he actually CALLED – and was communicative, I would’ve been open to that. Inability or refusal to communicate (at the outset?) is a deal breaker. Nexxxttt!

Here’s the abbreviated version of another guy. Don’t know how old he is but I’m guessing he’s in his mid-thirties. It’s somewhat irrelevant because I judge men based on other factors besides age. Anyway, I met him in ShopRite one night after a late-night workout at the gym. On our first date, he told me that his last relationship ended because his girlfriend complained that he smoked too much weed. Further he offered that it’s not something he can just stop. He needs help. And even further, his theory is that if people who work 9 to 5 jobs can go to happy hour when they get off work, he can do whatever he wants to after work as well. So if he gets off work at 7am (he works the overnight stock shift at the supermarket), he can smoke “L’s” (marijuana) when he gets off work! “She just kept nagging me and I couldn’t take that shit.” By the end of the date, I also found out that he had spent time in prison. (It happens – although initially he was pretending he had been away “at school” for a while.)  He also accused me of having a “boo” in Brooklyn cause ain’t no way I could just be going to see my mother all the time. Lately I’ve been too busy to see him and more importantly, uninterested in seeing him. Nexxttt!!!

NOW. After this brief rundown, my friend of twenty years still insisted that I must have a problem. Because a year and a half is just too long to be single. On one hand, I agree that I could probably do more to attract the type of guy I’m interested in dating. But at the same time, if I’m giving guys the pleasure of going out with me – and yes, they asked so they want the pleasure of my company – I really don’t owe them anything more, aside from respect and honesty and to be soft and sweet. The fact that a man says he’s really into me after a first date and wants to try to forge a relationship is not reason enough for me to oblige. I’ve settled in my past. NOW, I know which traits I’m most attracted to in a man. I know the type of man who brings out the best in me, and vice versa. I know that if I’m feeling some type of high with the man I’m in a relationship in, I’ll do everything in my power to keep that high going for him as well. I may have to work out and stay in shape. Maybe he’ll be turned on by my aggressive pursuit of my dreams. I may even have to wear my hair short, or cook healthy meals for the household, or help him build a business. If he’s building, and I’m building, and we’re building together… well that’s just sexy.

And ironically, it took dating an ambitious, motivated, confident 24-year old to help me realize the type of sustainable energy I thrive on in a relationship – and my capacity to give in return. We were on the high together. (But he’s another story.)

In the interest of not digressing too far from my phone call (wink), I’ll get back on topic. I had to end the conversation with him so I could get my lashes done at the MAC counter in Macy’s Herald Square. Afterwards, I sent him this text:  I agree with you. Now that I’m finally dating actively, I have to do more to attract the type of man I’m willing to date long-term. I know my type now – aside from physical qualities. I know for sure that I need someone outgoing and ambitious. The place I’m going tonight is upscale so that’s good! The key is also to have fun. I’m single so I should enjoy this time. And date. Woot!! It’s better than being unhappy in a relationship.”

His response: It’s funny according to your new standards I would’ve never made the cut as one of your boyfriends.”

Exactly. My standards are too high for him to meet. This would be a non-factor if he hadn’t broken up with his live-in girlfriend (and mother of his two young children) a couple of months ago and called me asking if I would consider having a serious relationship with him. I declined and he was offended. We’re supposed to go from friendship status to relationship status overnight? And what was his reason for leaving home? (He never mentioned this part – but for me, having sex with him was not an option either.) In knowing me for so long, this man has witnessed every serious relationship I’ve had – from the sidelines. And still, he asked to date me seriously. Problems and all?

What do you make of this situation? Ladies, have you ever had a male friend try to come off the sidelines, or judge your relationships (or lack thereof)? Fellas, is it possible to have a platonic friendship with a woman and not think of her sexually? How do you feel about having standards in dating? Is there any such thing as being single too long?

Categories: Dating Stories, Narratives

Tags: Advice, Dating, Emotional intimacy, friends with benefits, Friendship, Male friends, Relationships, Sex, Singles