Eyes wide open dating
September 28, 2019 12:24 AM   Subscribe

With some gentle prodding from my therapist, I'm back to online dating in my 40s (fwiw, I'm a woman in the US, looking for a man for LTR/marriage). In my past relationships, I fell pretty quickly for men, and could have done a better job of establishing what I wanted to get out of the relationship, rather than letting infatuation and insecurity push me to compromise my relationship goals. How do I make sure I'm asking the right questions up-front to make sure I don't fall too hard for someone incompatible?

AskMe has been a great resource to learn about what does early interest look like, dating tips, anxious attachment style, how to identify emotionally available men.

I'm in second -> fifth date territory, and from past experience, tend to go with the flow. Definitely enjoying the attention and flirting, but I would like to keep level-headed as well. What questions did you ask or what things did you do while dating to figure it out?

Assume I've already established the basics (wants a LTR or open to marriage, clear about kids/no kids, smoking/drinking/lifestyle etc), I'm looking for good questions that give you insight on character and shared values. What matters to me: being a team, shared level of commitment when it comes to family, support for each other's careers, being able to resolve fights like adults, no cheating, being on solid financial ground, compatible ideas on fun & enjoying life.

For example, Michelle Obama mentioned in her book that when her daughter Malia was sick in Hawaii, and Barack had a tough decision between going back to the mainland for a major state senate vote (and leaving her w a sick baby), he made the decision to stay, with no debate. That's an incredible example of how you approach a relationship as a team, but is there any way to learn that early on?
posted by anonymous to Human Relations (8 answers total) 12 users marked this as a favorite
The problem here is that most men cannot be trusted to be honest about this sort of thing early on in the dating process. I'm not saying they're consciously lying, but it's remarkable what you can persuade yourself of when possibly getting laid hinges on it.

One pure litmus test, though, which just about infallibly separates the discardable losers from the contenders, and which seems to get lied about less because the "bad" answer remains pretty socially acceptable, is the issue of earning a lower salary than you. How would they feel about being in a situation where you earned more than them? From men your age, anything other than simple matter-of-fact acceptance means someone worthy of no one's time.
posted by praemunire at 12:29 AM on September 28, 2019 [11 favorites]

I think dating gives you a chance to see not only how a person interacts with you, but how they interact with the world at large. Examples:

- How do they treat waitstaff at a restaurant? Do they give generous tips? Are they reasonable and allow for mistakes?

- What is their relationship with their family of origin? Do they speak highly of their parents? I once had a guy say that "all women are nags" and then look at me coyly, as if to see if I was in on the joke. I ignored it, thinking it was just something he was saying to get a rise out of me. But it turns out he really meant it.

- Do they do any volunteer work, or give to charity, express empathy for those in dire straits? Not everyone has to be Mother Theresa, but expressing empathy for people who are impoverished, helping others (i.e., stopping to make sure someone who's car has broken down is okay, holding the door for the person behind them, being tolerant of children at a family restaurant, etc.) can be a sign.

- Not being critical of others, regarding their weight, clothing choices, looks, etc. I used to be with a guy who thought it was funny to point out people to me, as if he were a walking People of Walmart spokesperson. Not cool.

- Are they well read? It doesn't have to mean they studied the classics, but one thing I like about my husband is that he reads books and articles on various subjects. They're not all subjects I'd read about, but we have overlapping interests, and will often discuss the local and national news with each other, and I'll ask if he heard about something, and he'll say he heard it on the news in the car, etc. Now it's a game to see if we can come up with a news story the other hasn't heard about first. We also share interesting articles with each other.

- How does he react when there is a crisis? One time, my daughter had lice, and she came up to me just as I was about to go on a dinner date (she'd shared a comb with a girl on a sleepover). My dating partner was somewhat put out, and at some point, I began to realize he only tolerated my kids, but wasn't invested in actually being a co-parent of any kind. This has happened more than once, and is a hazard of being a single/divorced parent. This can happen even if you have adult children who you interact with on a regular basis. Watch out for criticisms of your children, or other family members and friends, that is at the very least a sign of immaturity, and at worst a sign of controlling behavior (alienate and isolate, so you will be emotionally dependent on them). It's natural to be disappointed if a date gets canceled, but it's graceful to say, "I understand, let's get together when things are better for you," or, "how can I help?"

- How do you feel after you've been on a date? Happy, relaxed, looking forward to the next time? Tense, worried, wondering if they like you or when they'll call?

- Moving too fast. If a guy constantly texts you, calls you, moves too fast physically, those are not great signs, because it can indicate overstepping your boundaries (some call this love bombing). Ex.: sitting very close to you on a first date, putting their hand on your knee, making plans for you to meet the parents right away, showing up unexpectedly at your house with gifts, anything that makes you uncomfortable, pay attention to how you feel. Sometimes it feels good to be the center of attraction, but when it begins to take over your entire life, watch out. I once dated a guy, we went to see a football game at a local bar, and then he wanted me to go to brunch with him and his dad, and showed up at the house with flowers and candy at 7:00 at night, no phone call, and then insisted on the brunch thing again, when I'd told him no already. Then I just told him I wasn't ready to date other people. He wasn't a bad person, but I got the feeling that he'd have done this with any woman, not just me. He didn't take my previous hints, so I was forced to be blunt with him (and even then, I admit I made an excuse so as to not hurt his feelings).

- I think one of the best ways to get to know someone is to ask them about childhood stories, things they used to like doing when they were kids, or times they got into trouble, etc. My husband used to go climbing on a local bridge, I used to climb up onto the ice house and jump into the snow drifts, stuff like that. Family trips or outings, this can give you insight as to how they grew up, family values, how he interacted with his parents and siblings. It doesn't all have to be rosy, we all have baggage, but again, you're leaning about them, and they about you. This is a gradual process, of course.

- Views on housework, chores, etc. This is a big deal, because if you might eventually live together, who will do what? We go grocery shopping together, we do laundry together, and I do things he can't physically (scooping cat litter, he can't bend down far enough), and he takes away the trash to the dump on weekends. In the past, if I haven't felt like it, he'll go do the laundry on his own, or I'll do the shopping and he stays at home, but more often than not, we do those things together. He always offers to help. So how does he handle his household chores? Is he neat? Does he pay someone to clean, would he do it if you were together, or expect you to do it? Sometimes we'll pay to have our laundry done, it's a little extra money, but then we have time to do something else, and he'll go pick it up when it's ready, and we both put away our own clothes. My ex's would have never agreed to do that, too much money, etc., expected me to iron their shirts, clean the house, prepare the meals, and I'm not cut out to be a maid for a man at my age, been there, done that.

The most important factor is time. It takes at least 3 months to get over the "honeymoon phase" of dating someone, and longer to see if you are compatible longterm. I dated guys for a year or so, then something happened that really turned me off, or it just fizzled out. Often you'll know very soon, but if you like them and they like you, it still requires time to really get to know a person, because lots of life events can happen in one year, and you'll see how it goes during that time period.

FWIW, I didn't wait for my current husband to propose, per se. I told him it was important to me that we get married, I wanted the commitment, to know someone had my back in case I got sick and needed him to be able to make medical decisions (as opposed to my siblings or parents), and me the same for him. He went out and bought a ring the next day and proposed. Not as romantic as the movies, but he was all for it, and later said he didn't mind one way or the other, but he wanted to make me happy. 

(Also, he has said many times that he would be very happy if I earned more than he did. He had a good relationship with his mother, who was a strong woman, so maybe that helped, or maybe he's just an easygoing guy, IDK.)
posted by Marie Mon Dieu at 2:51 AM on September 28, 2019 [28 favorites]

I think it's difficult to know some things initially. You're probably not going to have a major disagreement in the first few dates, for example, and you won't know how he reacts in a fight. There's also something to be said for taking things slowly (I hate when someone grills me, job interview-style, on a first date to figure out if we're compatible). That said, it could be useful to ask about things like why his last relationship ended or how close he is to his family.

It might be useful to bring up a current challenge in your life, like something annoying at work, and see how he reacts- whether he's really listening, whether he seems to care and be genuinely sympathetic, whether he tries to mansplain a solution to you.

If you have time to take a long day trip on the weekend, the time in the car is a good way to have a longer conversation than you might otherwise. If financial goals are important to you, ask about that. You might also encounter some minor challenges on the trip like traffic or getting lost and see how he reacts, though most people are still on their best behavior at this stage and it might not be a full picture.

With one ex-boyfriend, I got sick before our second date (we'd met at a party, so it was our third encounter) and canceled, but he offered to bring me something, and ended up bringing me soup and a panoply of things from the drugstore even though he lived fairly far away. He also hung out with me even though I wasn't up to really doing anything. It told me a lot about who he was.

If you're looking for a serious relationship, it can be good to hold off on sex for a little while, because you can get a better sense of whether someone is interested in you as a person if they're also willing to wait.
posted by pinochiette at 6:15 AM on September 28, 2019 [5 favorites]

So I think of this in two ways: what I want and what I don’t want.

What I want is chemistry, shared values, good sex, etc.

What I don’t want is harder to articulate. But I am very attentive to red flags that show a distinction between what someone says and how they actually are. With one guy I liked, on date three, he made a homophobic joke and told me a story about a sexist joe he told someone else. I spent a lot of time thinking about it but realized I wouldn’t want to be around someone making jokes like that in the long term, so I stopped seeing him. With another guy I saw a few weeks, he would question why I made plans with friends even when he and I didn’t have plans. It was subtle but I ended it.

I have to say that I don’t necessarily agree that holding off on sex helps you know if someone is interested in you sincerely. You have to know yourself. Are you okay with having had sex with someone if it doesn’t work out? Sexual chemistry and compatibility is quite important to me. I don’t want to fall for someone and then find out our bodies don’t work together. I don’t want someone who thinks about sex a lot differently than I do.
posted by bluedaisy at 8:34 AM on September 28, 2019 [1 favorite]

To add to Marie's great list - What is his friend group like? Do their values align with yours? Are all of his friends straight cis-men? Do his friends treat/talk about women with respect? Are they mostly all in mature, stable relationships?
posted by Feminazgul at 9:10 AM on September 28, 2019 [1 favorite]

Words are good, but paying attention to behavior is far more accurate. Talk about past relationships.
posted by theora55 at 10:01 AM on September 28, 2019 [1 favorite]

I don't think it's fair to judge someone's relationship skills by whether they have a good relationship with their family of origin. Lots of people are dealt a really bad hand in that department. More fair is to see if they have a history of long, stable friendships.

I think a lot of relationship stability comes from three qualities that are either there or not: 1) sexual chemistry, 2) whether the person makes you laugh, and especially if they have the right kind of sense of humor that helps de-escalate a conflict, and 3) humility, which to me translates into a comfort level with acknowledging their own faults, apologizing when appropriate, and making sincere efforts to change behaviors that are problematic. These three are the qualities that keep you coming back together even when things are hard. Without them, life is grim, grim, grim.
posted by HotToddy at 10:05 AM on September 28, 2019 [6 favorites]

I was in a similar situation to you when I was 39. My therapist at the time urged me to listen to any alarm bells or red flags that came up during early dates.
I developed a few questions as well, the most useful of which was “What makes you want to get up in the morning?” The first two men I asked had literally no answer (and both proved to be losers). My now-husband was very honest and down-to-earth “The alarm clock, and my job so I can pay my bills.”
I wasn’t looking for a deep philosophical answer, just honesty.
posted by dbmcd at 10:40 AM on September 28, 2019 [6 favorites]

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