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30, Single, and Dating On a Timeline? Part 1: Could He Be the One?

Woman looking at a man

A single woman in her late twenties or early thirties may find herself looking to find a husband sooner rather than later. With her self-esteem on the line or her biological clock ticking in her ears, she may be on a one-year timeline, meaning that after one year of dating, she’s expecting a proposal of marriage.

How does a woman determine if the man she’s dating is on the same timeline?

A dating pace with the one-year timeline in mind must be established before the first date. But how does a woman convey this timeline without seeming aggressive or pushy? And how does she avoid being perceived as the active pursuer, but also find someone with whom to build a family?

Avoid wasting time with a man who doesn’t share your timeline without explicitly announcing to him, “I have a one year timeline!” which makes many women (and men) feel as if the woman sounds pushy – plus, it leaves the woman disappointed the man didn’t pursue her.

What should a woman do to increase her odds of finding someone with a similar timeline and goals of marriage and family? What are the signs that a man is on the same page as you? One thing to look for is that he shares the same level of what psychologists call “conventional thinking”: If you’re looking for a man who is likely to do traditional things like buy a ring, ask your father for your hand, propose marriage and set a wedding date relatively soon after the engagement, then understand that you’re looking for a man who is clear, organized and conventional. How do you know if he’s clear, organized, and conventional? Here are some signs:

● He asks you out clearly and directly.

  • He picks a specific time and place. It doesn’t matter the type of place or how expensive it is, but it must be specific. There should be no ambiguity about whether you’re going out as friends or not. You should know that he wants to take you out on a romantic date.He will pick up the check, at least on the first date. Traditionally, men pay at the onset of dating; whether it’s for coffee or a 5-star restaurant doesn’t matter. Even in a less traditional sense, the person who asked for the date or invited the other person on the date generally pays. By paying for the first date at least, he’s pursing you and underlining that he asked you for the date.

  • He will keep you in mind when choosing what to do on a date. The location will be convenient to you, and he may even suggest picking you up. He will ensure you get home safely.

● He has an organized quality to him – a sense of “onward and upward.”

  • He will initiate a conversation about dating exclusively. This is the first step towards entering the monogamous, exclusive space of marriage. If you’re hoping for a man who feels it is his role as a man to propose marriage, start by finding a man who sees is comfortable taking the lead on discussing exclusivity.

  • He is comfortable with social norms about male/female roles. This doesn’t mean that he expects you to put on an apron and cook dinner or clean the house; it means that he sees himself as a gentleman and a protector, yet also as strong and assertive. Being a little possessive of you, putting his arm around you, and being the one to initiate the first kiss all suggest that he espouses traditionally masculine behaviors- and if you’re searching for a man who will take the lead in defining the relationship and ultimately marriage, this can be a good thing!


  • Just because he pays for dinner and sees you home after dates, don’t assume this signifies he shares your relationship goals and timeline. I can’t tell you how many times I’ve seen beautiful, doe-eyed young women in my office who slept with a man after 3-4 nice dates and were then baffled when a committed relationship did not materialize. “But he always paid for dinner and saw me home!” they moan. It takes some work for me to help them see that while these behaviors are a nice starting point, they don’t tell a woman anything about his willingness or readiness for a future-oriented relationship.

    • Merely asking you to date exclusively isn’t enough – you must learn his intentions behind it. Just because he wants to date exclusively doesn’t necessarily mean he wants a future-oriented relationship with you. Maybe he wants a period of risk-free, unprotected sex; or maybe he wants a monogamous relationship now but is not interested in marriage within your timeline, or possibly at all.

    • Many women jump to conclusions when a man introduces them to his family. Just as it’s important to understand why he wants to be exclusive or see you home after dates, it’s important to remember a man could have many reasons for introducing you to his family: He could be getting pressure from his family to settle down, he could be close with his family and just enjoy sharing important people in his life with them, or he could want to share more about himself with you– all of these things are well and good, but they don’t necessarily mean that a man shares your relationship goal of finding a partner and getting married within the next year or two.

Navigating relationships in a world where traditional dating behaviors are less and less common poses many challenges for women who are searching for a traditional relationship where dating leads to marriage within a period of 12-24 months. If the man you’ve started dating isn’t clear and forthcoming about wanting an exclusive relationship leading to marriage, or seems to have trouble even defining when he’s asking you for a date, it could spell trouble for the pace and timing of the relationship. In my next blog, we’ll discuss what a woman can do to ensure her new romantic interest sees his future with her before she becomes emotionally invested.


Dr. Chloe's 10 Commandments of Dating


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