Dating for Grownups

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So, I’ve been dating. Actual dating, not just hanging out with someone occasionally, usually last-minute, like I did with the last guy. As I’ve mentioned many times before, I don’t really know how this is supposed to work, because my dating experience up until this point has been pretty much non-existent.

I met my ex-husband Kyle in college. We hung out at bars and at his fraternity house. When I dated guys before him it was similar – we’d meet up for drinks or watch a movie in a dorm room, sometimes with a weird roommate hovering a few feet away. All of these boys I knew prior to going out with them because we went to the same school, and we were close to the same age so we had some built-in topics to discuss, such as did we go to the last college football game, did we love or hate Dave Matthews Band and was Tupac still alive.

Now I’m going on dates with men I know only a bit about initially, and it’s a little intimidating to start from near-zero. These are guys who have been successful in their lines of work for 15-20 years or more. Kyle is successful, too, but I met him before he graduated, when we were more on equal terms. The men I’ve been out with have been married or have kids or have had long-term relationships that didn’t work out. They’ve dated more than I have. We go out to nice restaurants and they pay for me and I feel awkward wondering how hard I’m supposed to press the issue of offering to chip in.

Some things I’m struggling with:

1. I like to see the best in people, and also have heard enough stories about how happy couples met to know that attraction is not always instantaneous. So I have a hard time figuring out what to do about someone I enjoyed talking to but can’t yet imagine kissing. Do I keep going out with him and see if that chemistry develops, or assume that if it hasn’t happened by date two or three that it’s not going to materialize? I don’t want to string anyone along, but I also don’t want to give up on something too early if I otherwise like a man’s company.

2. Dating as a divorced parent means a lot of fretting over the calendar. I’ve met divorced dads who seemed interesting but we soon realized that we have opposite custody schedules. That’s not easy to overcome. Babysitters are expensive, y’all. I’ve also gone out with men who don’t have children who may not understand my limited availability (I share 50/50 custody with my ex) or that I might one day have to cancel on them because a child is sick.

3. Letting my guard down is not going to be easy. I felt like Kyle was manipulative, didn’t like me and was careless with my feelings. The longer we were married the more distrustful I grew of his intentions and feelings toward me. My short-lived dating experience since then was with a guy who lied and treated me as if I was the exact opposite of “the only girl in the world.” I’m almost more accepting of a man who is aloof or disrespectful because that feels normal, whereas when a man is open and kind and seems to genuinely LIKE me I grow suspicious. I think, “What is wrong here? Why is he being so nice? I don’t understand. He must be up to something.” I don’t want to deal with jerks anymore, so I need to be able to accept that some men will truly like me as I am, no devious strings attached and no plans to change me into someone I’m not.

4. My body-image. Not going to re-hash it, but I have issues with feeling confident over how I look, and it’s hard for me to accept compliments. When a man tells me I’m pretty I have to force myself to say thank you instead of argue with him about all the flaws that make me NOT.

Let’s not even get into how much texting freaks me out (I don’t like texting someone I don’t know well enough to understand if they’re joking or not about things) and that Google is awesome when I want to use it for date research but not awesome when I think of others using it to find me.

What I’m enjoying:

1. I like conversations and learning about new people, period. Talking to a person I’ve recently met fascinates me – I love to hear about their experiences and what makes them who they are. I don’t get nervous easily and I’m glad to have met even the men I am not interested in dating. Wait, I take that back, there was one oddly hyper guy who kept smacking my arm and back for emphasis while taking – I could have done without him, but even that was a learning opportunity, right?

2. I’m getting outside of my bubble. When someone asks me out, I ask him to recommend a place to go. I think it says something about the person and I also get to try new foods and atmospheres. I guess this could go under “Struggles,” too – I’ve been eating out WAY too much at restaurants and am going to gain so much weight I’ll outgrow my cute clothes and will never want to date again.

3. I’m learning to be gracious instead of constantly self-deprecating. See above – I’m trying to simply smile and say thank you when a compliment is bestowed upon me. My natural instinct is to yell, “Shut up,” or “You’re such a liar!” but those might sound a tad abrasive and ungrateful.

4. The hope of clicking with a new prospect is kind of exciting. There is one guy in particular who’s piqued my interest the most and while I’m not getting too ahead of myself, I find myself really looking forward to seeing him again, or smile bigger when I get a message from him. That’s kind of fun, right? Of course, I realize things may just fizzle before they go anywhere, and I will survive, but I think it’s the anticipation of something possibly wonderful happening that keeps men and women dating again and again instead of giving up in favor of a life of solitude, litter boxes and streaming video subscriptions.

This dating game is in the early stages – I made a decision a while ago to start accepting dates and the opportunities have come trickling in, which is almost surprising to me (my lack of self-confidence comes into play here again – when someone asks me out my first thought is, “Why ME?”) but I’m staying relaxed and not taking anything too seriously. I did learn my lesson about blogging about someone I’m currently dating, so I won’t be doing that again, but maybe when enough time has passed I’ll dish out some specifics on the duds and the good ones.

So far it’s just bewildering enough that I’m dating at all. Dating grown ups, even.

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Image used under creative commons license from the Boston Public Library.

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