Understanding Relationship Compatibility in Early Dating
April 17, 2025
(A version of this was previously published on Sixty and Me.)
The biggest mistake women make in midlife dating is staying for a long time with the wrong person. If you’re lonely, you are susceptible to picking badly, and then staying put, hoping it will turn into a successful relationship if you’re patient or work hard enough to fix him. I want to prevent that!
I want you to be analyzing true relationship compatibility from the very first interactions!
Why is compatibility in dating important?
Compatibility is where most relationships go off the rails. Post-breakup, most people admit they knew all along what wasn’t going to work. But early in dating, people confuse chemistry with real alignment, and before they know it, they’re months (or years, eek!) into a long-term relationship with someone whose life goals, habits, or values don’t actually match up with theirs. And that leads to resentment, frustration, and a lot of wasted time.
Here are the things I strongly recommend you look at within the first 3 dates:
Is It a Compatible Relationship? How Much Togetherness Works for You?
You must, more or less, agree on how much time together you actually want to spend. Some people are perfectly happy in long-distance relationships, and others want to be together every single day. If you don’t sync up here, I’d call it a fundamental mismatch and bad news for a lasting relationship.
I only found out my next-door neighbor was married when her husband died! Why? Because they lived across town from each other! Even though they lived in the same city, they were all about freedom and independence until the very end. Don’t assume your romantic partner has the same long term desires for time together and interdependence as you do!
I have worked with numerous women over 50 who are perfectly happy to continue living alone, even in a highly compatible relationship with plenty of common ground. Some people are satisfied with long-distance relationships and meeting for travel and special events, and some people want to see their partners every day for long periods, and everywhere in between, of course--mutual understanding makes the relationship work.
The thing about aging is that we learn to do things on our own, to be independent, to make our own decisions, and to fill our lives with wonderful people and activities. Please do not assume that finding true love necessarily means changing all that, it doesn’t have to.
Finding Common Ground: Activities for Couples
Then there’s what you actually do together. Some couples want to do everything—dinners, events, hobbies—while others are fine keeping things separate except for sex or the occasional plus-one situation. Different interests are fine, but if you have a strong preference, you need to be upfront about it and honest about your long-term goals.
Ask yourself:
- Are you only looking for a “plus one”, or do you want to spend a lot of time with the right person?
- Do you want to travel together?
- Do you prefer separate hobbies or shared activities with mutual support?
- What activities “must” your partner share (golf, pickleball, cooking)?
- Are meals, TV time, or certain social outings and common interests important to do as a couple?
- What involvement do you desire as far as spending time with each other’s families?
If you don't have true compatibility in these areas, this is what you will fight about and eventually what will break you up. Talk about it early on!
Compatible Couples Agree on Frequency and Style of Communication
Are you a texter? Do you like to phone or video chat? How many dates a week feels like the right pace? What does effective communication mean to you?
These are not taboo topics to bring up at the beginning of a relationship with a potential partner, to ensure that each of you gives the right kind of and amount of attention to the other in the long haul.
Two of the biggest complaints I hear from women daters over 50 in a romantic relationship are that the man they are dating communicates too much or too little. They are not mind readers, and they need to be trained in how you like it in order to be a compatible partner and engage in mutual respect.
Please assess early on if it will be easy and enjoyable to maintain communication between the two of you.
Conflict Resolution: Can You Talk It Out?
How you resolve conflict in a healthy relationship is just as important as how much fun you have together. Do you both agree that honesty is the best policy, or is one of you the type to sweep things under the rug and hope problems disappear?
Some couples never really fight because they know how to work through things respectfully and proactively. Others go from zero to disaster over the smallest issues. The key questions here are:
- Do we both agree to address issues rather than avoid them?
- Are we on the same page about truth-telling vs. withholding information?
- Can we navigate difficult conversations without them escalating?
- Do we have a format or ritual for bringing things up so that it’s not so scary?
If you and your partner can’t even agree on how to handle disagreements, good luck staying in a committed relationship with a deeper connection.
From Initial Chemistry to Long-term Intimacy: Are you Sexually Compatible?
And let’s talk about sex. If your sex drives or preferences are wildly out of sync, you’re in for a rocky road. Sometimes people can adjust, but if one of you wants sex three times a week and the other is fine with once a month, resentment is going to build.
My husband and I had different libidos when we first got together, but we found a balance that worked for both of us. You do not need to like the exact same type of sex or frequency, but you have to be close enough for it to work, you have to feel physical attraction, and there has to be an emotional connection. And if one of you has a fetish, kink, or otherwise “extraordinary” desire, or STD, the other one gets to vote (in advance of sex!) if it’s a deal breaker or not!
Ask yourself:
- Do we have similar values when it comes to sex frequency?
- Do we both have an open mind for discussing boundaries and preferences?
- Are we being completely transparent about sexual health?
If you’re avoiding these conversations, that’s a red flag in and of itself.
Monogamy: Do you have a Shared Desire and Definition?
Monogamy means different things to different people. Some are okay with a little flirting, while others think even texting an ex is crossing a line. You need to get clear on what monogamy looks like to both of you—and if you’re dating multiple people at once, how much transparency are you giving each other? If your definitions don’t align, that’s a major liability.
The Big Long-Term Commitment Liabilities: Health, Money, Exes, and Geography
Beyond the basics, there are certain life realities that people try to ignore but absolutely shouldn’t. Health issues are a given—if you’re dating after midlife, both of you are going to have some. But what if one of you has a serious condition that requires constant care? What if your partner has a lifestyle-related health issue they refuse to address? You have to be honest with yourself about what you’re willing to take on.
Finances are another huge one. People lie about money all the time, especially in the early stages. But money plays a role in nearly every aspect of a relationship—from lifestyle choices to retirement plans—so if you and your partner have completely different attitudes about it, that’s a red flag. You don’t need to have the exact same financial situation, but you do need to be able to talk about it openly and honestly.
Other areas that can cause major relationship problems:
- Exes and lingering attachments: Are they still in the picture? Do they demand too much attention?
- Geography: Will someone be willing to move? Are they truly open to relocation, or just saying it?
- Work and family obligations: Are they always going to put something else ahead of your relationship?
At the end of the day, compatibility in dating isn’t just about chemistry. Attraction is great, but it won’t save you if the fundamentals don’t align. These conversations might feel heavy for a third or fourth date, but trust me, avoiding them only leads to disappointment later. If you’re serious about finding the right match, be honest about what you want—and expect the same in return. That’s how you date like you mean it.
What does this all mean?
Ladies, the best way to avoid cynicism and resignation about dating is to do it with your eyes wide open! That means paying attention to these areas of alignment before agreeing to be monogamous or having sex with a new partner.
Early dating is the best time to explore these matters openly with someone new and really determine whether or not it’s a good match. I suggest only 3 dates to get the job done, and if you want to know more about how to get it all done that fast, watch my free webinar “3 Secrets to Finding and Maintaining Healthy Love.” See you there!
Love,
Frequently Asked Questions about Understanding Relationship Compatibility
When is the right time to bring up serious compatibility topics?
By the third date, you should be discussing things like lifestyle, communication habits, and long-term goals. It doesn’t need to be an interrogation—just curious, open conversation to see if your values align.
What if we have great chemistry but want very different lifestyles?
Chemistry fades. Incompatible lifestyles don’t magically align with time. If you want daily connection and he wants occasional weekend check-ins, it’s unlikely to work. Be honest early before you get too emotionally invested.
How do I know if we’re sexually compatible before we’ve had sex?
You talk about it. Discuss frequency, boundaries, preferences, and expectations around intimacy. If that conversation feels awkward or avoided, that’s already a red flag.
Is it wrong to ask about money or health issues early on?
Not at all—these are major long-term realities. You don’t need a full financial statement or medical record, but you do need transparency about how those topics might affect your future together.
What if he avoids conflict and says he “hates drama”?
That’s a sign he might not have the tools to navigate relationship challenges. Healthy relationships require open communication, even when things are hard. If he shuts down or deflects serious talks, that’s not compatibility—it’s avoidance.
Love,