Why dating in your 30s is hard
As Sara and I browsed the Union Street boutiques searching for the perfect Little Black Dress for her niece’s wedding in a few weeks, we couldn’t help but overhear two attractive 30-something blondes nearby. Their conversation sounded eerily familiar to ones Sara and I had had ourselves not too long ago.
“I swear, I just don’t get dating anymore. It’s impossible to be what guys are looking for. You’re screwed if you’re too direct because then you’re come off as cold. If you’re too aloof, you’ll seem like a bitch but if you’re too eager then you’re too needy,” one lamented.
“You’re so right.”
“Plus, you can’t talk about your ex-boyfriends because you’ll sound bitter, but you can’t talk about the future either because then it’s like you’re fishing around for commitment or something,” she continued. 
“It’s nothing like when we were in our 20s!”
“But, we’re not even old!”
“I know but it feels like it. Like that guy I went out with last week, you know? When I told him I was 34, it was like I could see him doing the baby momma math on me — ‘Well, if we start dating now, then get engaged and married, it will be about two or three years and we’ll have to have a baby right away because she’ll be too old and I’m not ready yet.’ It’s depressing!”
Wow — even I was getting depressed listening to them! Now, when Sara and I were bemoaning dating post-divorce, we were in our 40s, fresh out 15-year marriages, and moms. We were not baby-making machines anymore. We already had kids, and most of the guys who were interested in dating us were mostly divorced and had kids, too; the guys our age who didn’t were looking for younger women, not us (well, except for a hookup). Coordinating custody schedules was challenging, and single parenting and working full time was exhausting!
Still, I remember thinking how much easier it might be to find love again if I had gotten divorced in my 30s, not my 40s. Listening to the blondes, however, I’m realizing that may not be the case.
But, the young blonde (yes, 34 is young!) was right — once you’re out of your 20s, dating is an entirely different beast. Dating in your 30s gets a lot more complicated because of kids — either you have them, which limits your dating ability; you don’t have them but you want them, which puts you on a tight time-track for fertility; you don’t have them and you don’t want them, but you may have to reject a lot of good guys who do want to have kids; or you have them and you want more of them, which, again, means you may be facing fertility issues.
Whoever said kids put a strain on a marriage has no idea how hard it is to date with or without kids as a 30-something!
All of which means — you better enjoy dating in your 20s because if will never be as carefree and fun or offer as many options again! Ever. OK, that’s not fair; I had fun dating post-divorce and, after all, I met Sean in my mid-40s and that’s been very great. A few of my middle-aged friends have met great guys and women, too (although none has remarried). But, let’s face it — dating when you’re older is really, really different, especially if you’re looking for a relationship and not just casual sex. And sometimes, it downright sucks.
What’s your dating story at your age?
Photo © Angelika Bentin – Fotolia.com
Is it really that bad to have sex on the first date?
When I saw that my friend Dan had changed his Facebook status to “in a relationship,” I just had to give him a call. But first, I clicked on the profile of the gal he was in a relationship with. Much to my surprise, she looked nothing like I would expect him to be with, based on his former girlfriends. She’s pretty, but in a sweet girl-next-door way.
What had happened to the Dan who always fell for babes who looked like they made their living swinging naked on a pole at the local strip club?
So I called him, and yesterday we meet over some beers.
“Should I be worried about you?” I asked.
“Why? Do I look sick?”
“No. Actually, you look happy.”
“I am happy. I’m in love.”
“But she’d not your type!” 
“Who? Kat, did you …”
So of course I fessed up on my snooping.
“Katy is absolutely my type! She’s sweet and smart and a total babe. You had me pegged all wrong.”
“I had you pegged by what you usually dated — they may have been smart and maybe even sweet but they were way beyond ‘total babes’ — they were, you know, skanky.”
“Well, just like women are drawn to bad boys, we guys are drawn to sluts. We can’t help it. But, no guy wants to to be boyfriend to that. We just want to …”
“Have sex with them.”
“Bingo.”
“So a girl who gives it up on the first date?”
“Uh, probably not the bring-home-to-the parents type. But you know that.”
“But, women don’t trash a guy because he wants to have sex on the first date. We expect a guy’s going to at least try!”
“Guys aren’t woman and women aren’t guys. Thankfully.”
“So, then why do women give it up so easily and dress so trashy?”
“Kat, I think you would know that better than I.”
And he was right, I guess.
Women like to dress provocatively; I know I do. It gets attention from guys, and I like to play up my femininity. But as I age I know there’s a line between looking sexy and looking trashy; older women who try too hard to look young cross that line in a tragic way. You can get away with some trashiness when you’re 20-something, but you actually don’t have to do too much to look sexy at that age; I wish more young women understood that!
But when it comes to sex, I know why some women give it up easily — they just want to have some fun, just like guys do. I’m not going to say it’s empowering — God, I’m really beginning to hate that word! It’s just that some women don’t have any hangups about casual sex. But a whole lot more women do, and they have sex freely and easily because they’re hoping it will lead to a something, probably a relationship. Sometimes it does but not necessarily with someone we want to be with for the long haul. Even if we don’t put out on the first date, Date 3 comes along and …
But, if guys don’t particularly want to have relationships with women who dress like they’re working the street corner and who give it up too soon (and I’m not 100 percent convinced I know when “too soon” is), then why do so many women go the skanky route? If guys like the chase then shouldn’t more women who are interested in having a relationship hold out from having sex with a guy for as long as they can — or at least until they recognize the guy’s not in it just to score?
Of course, if a guy dumps a woman after sleeping with her on the first date, he probably wasn’t too serious about wanting a relationship in the first place. It shouldn’t be a deal-breaker, or should it?
- Guys, what do you think of women who have sex on the first date?
- Do you always try to score on Date No. 1?
- Are skanky women lookers and not keepers?
- Gals, do you have sex on the first date? Why or why not?
- Do you dump a guy who tries? Do you have more respect for a guy who doesn’t try?
Photo © dimis – Fotolia.com
Dealing with the ex for better or worse
“You won’t believe who I ran into the other day,” Sara said as we stood in line to board the ferry to the Giants game.
“I hope someone worth running into, like Lincecum or whatever actor’s filming somewhere around here.”
“No, someone much more interesting — Todd’s ex.”
Todd’s the OkCupid guy Sara’s still sweet on and vice versa.
“Oooh, what’s she like?”
“Nothing like I thought she’d be like, which, of course, is all based on what Todd told me about her. She’s not at all psycho. She actually seemed like she could kick back a cosmo or two with us, you know? I like her.” 
There are a few weird experiences when you’re divorced — meeting your ex’s new love, having your new love meet your kids, meeting your new love’s kids, and meeting your new love’s ex.
I always listen to a guy talk about his ex with a grain of salt — there’s his version of the truth, her version and then “the truth,” which is likely some mash-up of his truth and hers.
Of course, some exes truly are total nightmares and they can ruin a budding love affair, as Sara discovered when she fell in love with Jeff many months ago but ended it because she couldn’t imagine a future with Jeff and his psycho ex. What happens, though, if you kind of like his ex and he still feels negatively toward her; can you be a positive thing in their relationship — especially if kids are involved.
And at what point do you ask to meet the new love — if you even should ask, that is. If you know your ex has a serious squeeze, one who’s spending time with your kids and developing a relationship with them, do you have a right to ask to meet her? Do you hang around places you know you might accidentally on purpose bump into her, or do you just let it go? And, do you make sure your ex meets you new sweetie?
None of these are questions we even think off when we’re divorcing — there are bigger issues then, right? Funny, but then they start to play a role in our new life, and now we’re forced to think about them whether we want to or not.
I’m not saying it’s better to stay married, but it sure can be less complicated!
- What has been your experience with either past or present exes?
- What has been your new love’s — past or present — of your ex?
- Do you believe you should meet your ex’s new love if it looks serious and you have kids?
Photos © Angelika Bentin – Fotolia.com
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