12 Things to Consider Before Dating an Older Man

Co-authored by Jonathon Aslay and Hannah Madden

Last Updated: November 26, 2025 Fact Checked

If you’ve been on the dating scene for a while, you may be getting tired of the immaturity of people your own age. Setting your sights on an older man might seem like a logical next step, but it’s important to weigh the pros and the cons before you pursue an age gap relationship. Read through these benefits and drawbacks of dating an older man to make the decision that’s right for you and your love life.

1

Pro: They’re usually more mature.

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Guys your own age haven’t had a ton of life experience. If you often find yourself wondering why the guys you date just want to go out and party all the time, dating an older man might be for you. If you get called an “old soul” a lot, you’d probably have a lot in common with someone a little older.^{[1]
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- Keep in mind that this is usually, not always. Even older men can be immature sometimes.

2

Con: They can be a little possessive.

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Older men might be more worried you’re going to be unfaithful. This is especially true if you still go out to bars and clubs with people your own age. If he’s a jealous person, his possessive nature could become a problem in your relationship.^{[2]
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- Jealous behavior can happen at any age. If your partner is controlling where you go, who you talk to, and when you can go out, it may be time to end the relationship.

3

Pro: They’re usually financially stable.

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He’s had a long time to work and save his money. While guys your age might still be working for minimum wage or taking college classes, older men are more likely to have some money in the bank. Usually, they can provide for you a little better than younger men can.^{[3]
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- This is another stereotype that isn’t always true. Older men can definitely be in debt, and they aren’t always rich just because they’re old.

4

Con: They might not want to take you out very often.

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Older men have already lived out their partying days. If you enjoy staying out until the wee hours of the morning, he might not always want to join you. It could turn into a point of contention if he’s constantly bailing on plans or he just wants to stay home and watch TV.^{[4]
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- You also might not like going out to the same places. If you prefer the club scene and he likes quiet, candlelit dinners, it could be an issue.

5

Pro: They often have more sexual experience.

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They’ve had years of experience you might not have had. Generally, older men know what they like in bed (and they might know what you like, too). While guys your age are still figuring it out, an older man has already experimented enough to know what works and what doesn’t.^{[5]
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- On the other hand, he might be less open to trying new things with you. Older men tend to get stuck in a rut of what they like and what they don’t.

6

Con: He might come with a lot of baggage.

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If he’s been married, there’s an ex in the picture (and probably kids). You might have to see his ex at family events or when they drop the kids off. Your boyfriend might also have to pay child support or share custody of his children, if he has them. It’s just one more thing to consider when you think about dating an older man.^{[6]
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- His ex won’t necessarily be mean to you, even if they had a messy divorce. However, it is a possibility.
EXPERT TIP

John Keegan
Dating Coach
John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan
Dating Coach

On the bright side: he might have a lot of emotional intelligence. Emotional intelligence develops with experience, which an older man with "baggage" with definitely have.

7

Pro: They’re usually ready to commit.

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Older men tend to know what they want. You probably won’t have to deal with the wishy-washy “what are we” conversation—an older man will let you know if they want to get serious or not.^{[7]
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Jonathon Aslay
Dating and Relationship Coach

Expert Interview} If that’s something you want, getting in a relationship with someone older might be a good idea.^{[8]
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Pew Research Center
Nonpartisan thinktank conducting research and providing information on public opinion, demographic trends, and social trends

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- On the other hand, he might pressure you into taking steps you aren’t ready for yet (like marriage). If you aren’t ready to commit, it might not be the relationship for you.

8

Con: You might have to deal with criticism.

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Your friends and family members might have something to say. If your relationship is getting to the point that you’re introducing him to the people in your life, be prepared to defend the age gap if you need to. Well-meaning people are generally wary of large age gaps in relationships.^{[9]
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- You can get people not to worry by telling them about how deep your connection is and showing them that it’s a loving, respectful relationship.
- Wondering what wikiHow users have to say about age gaps in relationships? Check out wikiHow's “What's considered a big age gap in relationships?" forum.

9

Pro: He’ll probably get along with your parents.

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When you first introduce them, it might feel a little funny, but once they chat for a while, they’ll probably be just fine together. If you’re getting to the point that you want to bring him home to the parents, you may want to warn your mom and dad ahead of time that he’s a little older.^{[10]
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10

Con: You two might not have a ton in common.

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The age gap might come with an interest gap. Maybe he likes watching movies from the 70s, while you prefer reality TV. Or maybe you like to go out and get active in nature, while he prefers lounging around the house. Relationships are built upon your common interests, so it’s important to have a few things you both like to do together.^{[11]
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Erika Kaplan
Matchmaker

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- Of course, this isn’t all bad—it’s an opportunity for you two to teach each other about what you like to do.
- If you have a lot of the same values, that's more important than knowing all the same pop culture references, so don't let that hold you back if you really care about each other.^{[13]
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11

Pro: He most likely has a stable job.

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No more job hopping for this guy. If he’s past his 20s, he probably knows what he wants to do and is sticking to it.^{[14]
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Jonathon Aslay
Dating and Relationship Coach

Expert Interview} Unless you find him in the middle of a mid-life crisis, he’s probably got his career locked down.^{[15]
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- Of course, there are some older men that find it tough to hold down a job or pick a career and stick to it. However, they’re not very common.

12

Con: You might have different goals in life.

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You might just be getting your life started while he’s ready to retire. If you want to travel the world or advance your career while he wants to move to a remote location in the woods somewhere, your relationship might have issues. It’s important to talk about your long-term goals early to make sure you two are on the same page.^{[16]
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- Similarly, he might be ready to settle down and start a family while you’re still wanting to go out and party.
- Reader Poll: We asked 512 wikiHow readers how they navigate differences in life stages and priorities in an age gap relationship and 67% of them said open and honest communication about individual goals and expectations. [Take Poll]

Join the Discussion...

What's considered a big age gap in relationships?

WikiGopherCaster108

i'm a 23-year-old woman dating a 32-year-old man, and i've gotten some negative feedback from people who say this age gap is too big. so it has me wondering, what do you all consider "too big" of an age gap? and what are your best tips for making our love last despite our age difference and other people's opinions?

Attract and Date an Older Man with this Expert Series

There's nothing wrong with an age gap in an adult relationship as long as both people are on the same page. Learn how to attract and date the man of your dreams with this expert series.

1

12 Things to Consider Before Dating an Older Man

2

Date an Older Guy

3

How to Handle an Age Gap in Your Relationship

4

13 Explanations for Why Older Guys Like Younger Women

5

Why Am I Attracted to Older Men?

6

Attract an Older Guy

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If you’re under 18, dating an older man is illegal. Wait until you’re a legal adult to start dating someone older than you.

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The advice in this section is based on the lived experiences of wikiHow readers like you. If you have a helpful tip you’d like to share on wikiHow, please submit it in the field below.

Step back. Take off your rose colored glasses. Write down the pros and cons, because the cons are not going to change. If the relationship makes you smile more often than you frown, then have a beautiful life!
Baggage isn't always a bad thing, and older or younger partners can come with baggage. As long as they have both gotten past it, that's what counts.

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