DATING FORUM

Question

I’ve been dating a young woman for 11 months and have fallen deeply in love with her. I can honestly see myself marrying her. But our relationship has reached a crossroads, and I’m struggling with whether I should continue waiting for her or finally walk away.

When we began dating, I knew very little about her past. About four months into our relationship, she told me that she had struggled with drugs and alcohol and was participating in a 12-step recovery program. She also came from an abusive household. I never judged her for any of this. In fact, I admired her tremendously for acknowledging her struggles, hitting rock bottom, and finally taking the initiative to rebuild her life.

She is now 13 months sober and working through her recovery program. She is currently on Step Four, which involves taking a personal inventory and examining painful experiences from her past. Her sponsors and mentors have advised her to concentrate on her recovery and complete additional steps before becoming seriously involved in a relationship.

Throughout our 11 months together, we’ve grown very close. She introduced me to her parents, who have been extremely welcoming. They’ve told me that I’m a breath of fresh air compared with some of the men she previously dated. Her mother even encouraged her not to let a good man like me go.

She has told me that I’m one of the best men she has ever dated. We never officially called ourselves “boyfriend and girlfriend.” We’ve been companions who date regularly, but without a defined relationship status. The age difference between us is 16 years and eight months. Neither she nor her parents seem concerned about it, and I’m comfortable with it as well.

I’ve tried to show her how much I care. I bought her soup when she was sick, spent time with her, and tried to be supportive as she works through her recovery. I’ve been patient because I understand she has been through a great deal and recovery requires time. However, after 11 months, I want to know whether we are moving toward a serious relationship or whether I’m investing my heart in something that may never progress.

Unfortunately, I’ve made some mistakes along the way. The first incident occurred in April, when I met her mother. I asked her for permission to exchange phone numbers with her mother, explaining that I wanted to have some way to contact her in case of an emergency. She said no. Later, when she was not in the room, I approached her mother and gave her my number anyway. My thinking was that, given the length of our relationship, it would be sensible to have a way to reach someone close to her if something happened to either of us. When she discovered what I’d done, she was extremely upset.

The second incident involved my intention to buy her a promise ring. I texted her mother about it, and she found out. This upset her as well.

Then came September 15. After dinner together, I gave her a photo album containing pictures from our dates over the previous 11 months. I wanted her to see the memories we had created and understand how meaningful our relationship was to me. I asked whether she still cared about me and whether she continued to see a future for us. She said yes. She told me that I was one of the greatest men she ever dated. But she also said that she was not on the same page as I was. She was not where I wanted her to be, and she was not ready to be in a relationship.

I was confused. If she cared about me and saw a future with me, why was she not ready to take the next step? After nearly a year together, I felt that we should have a clearer understanding of where we stood. I told her that while she was away in Israel with her father, I had approached her parents to ask for their blessing. I want to emphasize that I was not proposing marriage or planning an immediate engagement. I simply wanted their blessing because I was serious about her and envisioned a future together. She was furious. She told me that I had crossed her boundaries for the third time and she needed a break from me. She said she needed to pull back and have some space to think.

Three days passed with no contact. On September 18, I sent her a bouquet of flowers that cost $350. Within 24 hours, she responded. However, her message was not the response I had hoped for. She told me that I seemed insecure, that she was turned off by my repeated boundary violations, and she needed space.

I admit that I’m feeling insecure about this particular relationship. I’m not generally an insecure person. I am confident in my professional life and in most other areas. But it’s difficult to invest nearly a year in someone, develop deep feelings, and still not know whether you’re actually building a relationship together.

I’m miserable. I love this woman, and I want to marry her. I know her parents like me, and I believe I have treated her with kindness and respect in many ways. I also recognize that I crossed boundaries, even though my intentions were good. So, I am asking, should I fight for this love, or should I stop chasing her and wait to see whether she reaches out to me? How long should I wait for someone who says she sees a future with me but is not ready to be in a relationship? Am I being impatient, or is it reasonable to want clarity after 11 months?

Sincerely,

A Confused and Heartbroken Man

Response

First, I want to acknowledge how painful this situation must be for you. When you care deeply about someone, envision marriage, and believe you have found a person with whom you can build a life, uncertainty can be excruciating. You’re wondering whether the relationship you have invested almost a year in has a future. That is a normal concern.

However, I believe that the most important question here is not whether you should chase this woman or wait for her to come back. The real question is whether the two of you are emotionally ready for the same kind of relationship, and whether you can learn to respect each other’s needs without losing sight of your own. There are several important issues to examine, because this situation is more complicated than a woman who is afraid of commitment or a man who is impatient to get married.

Let us begin with something you may not want to hear. A woman can genuinely care about you, enjoy your company, appreciate your kindness, and believe you’re a wonderful man without being ready to commit to you. When she tells you that you are one of the best men she has ever dated, she may mean it. When she tells you she sees a future with you, she may mean that, too. But neither statement necessarily means that she’s ready to enter a committed relationship. It is possible that you are on different pages. You’re looking toward marriage while she’s concentrating on recovery. You’re thinking about what the two of you can become while she’s telling you that she’s not yet ready to become that couple. This difference matters.

It is tempting to believe that if someone truly loves you, they will eventually overcome their hesitation. Sometimes that happens; sometimes it does not. Love does not automatically resolve emotional struggles, and a promising connection does not guarantee compatibility in timing, expectations, or readiness.

You cannot determine her readiness by how warmly she introduced you to her parents, how many dates you have shared, or how much she appreciates your gestures. The clearest information you have is what she has actually told you: she is not ready for a relationship. You need to take that statement seriously rather than treating it as an obstacle you must overcome.

You mentioned that she is 13 months sober and working through a 12-step program. You admire her for taking responsibility for her past, and that is commendable. Recovery takes courage. It also requires sustained attention, honesty, self-examination, and the development of healthier ways to cope with emotional pain. For someone who has struggled with substance abuse and experienced abuse within her family, establishing emotional stability and healthy boundaries may be particularly important.

Her sponsors and mentors have recommended that she continue concentrating on her recovery before entering a serious relationship. Their advice deserves consideration, although the precise recommendations of any program can vary from person to person. You do not have to agree with every recommendation she receives. However, you do have to respect her decision to follow that guidance.

You may believe that a loving relationship would provide her with additional stability. You may feel that your patience, loyalty, and support could help her grow. Perhaps it could. But that’s not a decision you can make for her. Nor should you assume that becoming her boyfriend, chassan, or husband would help her recover more successfully. A romantic relationship can be loving and supportive, but it can also introduce new emotional demands, expectations, disappointments, and stress. She may believe that she needs to establish a stronger foundation before taking on those responsibilities.

Whether you would make an excellent partner is one question. Whether she’s ready to have a partner is another. You can be the right kind of man and still be involved with someone who’s not ready for the relationship you want. And that distinction is important because you must not turn her recovery into a project in which your patience and devotion are expected to produce a particular result.

She does not owe you a commitment because you’ve stood by her. You, in turn, do not owe the relationship an indefinite amount of waiting simply because she has struggled. Both of you have a right to make decisions that protect your emotional well-being.

Now we come to the part of your letter that I believe requires the most honest examination. You acknowledge that you crossed her boundaries three times. I appreciate that you’re willing to admit this, because self-awareness is essential in any healthy relationship. However, you repeatedly explain why your intentions were good. You wanted her mother’s phone number in case of an emergency. You wanted to buy her a promise ring because you were serious about her. You asked her parents for their blessing because you envisioned marriage. None of those intentions are inherently bad.

In a different relationship, exchanging numbers with a partner’s parent, discussing a promise ring, or asking parents for a blessing might be welcomed as thoughtful, loving gestures. But context matters.

The first time, you asked her whether you could exchange numbers with her mother, she said no. You then went ahead and gave her mother your number anyway. The problem was not that you wanted to be available in an emergency. The problem was that she had already expressed a boundary, and you decided that your reasoning was more important than her answer. The second time, you contacted her mother about a promise ring. Given the previous boundary violation, this was another step involving her family in a relationship that she had not agreed to formalize. The third time, when you approached her parents for their blessing, you did not first establish with the young woman that she wanted the relationship to move in that direction. You viewed your actions as expressions of love and seriousness; she experienced them as repeated disregard for her wishes.

Both perspectives help explain what happened, but they do not carry equal weight when it comes to consent and boundaries. Once someone has clearly communicated a limit, good intentions do not give us permission to override it. A loving gesture is only loving if it respects the person receiving it. A promise ring is not merely a piece of jewelry. It communicates a degree of commitment. Asking parents for a blessing can carry significant emotional meaning, particularly when the relationship has not been defined. Even a seemingly practical exchange of phone numbers can become intrusive when the person involved has expressly said no.

Your intentions may have been sincere, but the effect of your actions was that she felt her feelings were being disregarded. You cannot repair that by making an even bigger gesture. In fact, the more you try to demonstrate your love through increasingly significant gestures, the more pressure she may feel. The lesson here is not to stop being thoughtful or romantic. It is to learn that thoughtfulness must be guided by listening.

I understand why you sent the flowers after three days of silence. You were hurting. You wanted to reconnect. Perhaps you hoped the bouquet would communicate what you could not adequately express in words, that you loved her, that you were sorry, and you didn’t want to lose her. But you need to consider how she may have experienced it. She told you that she needed space. She explained that the repeated boundary violations had turned her off. Three days later, she received an expensive bouquet.

You may have intended it as an apology, but she may have experienced it as another attempt to change her mind before she had the distance she requested. The price of the flowers is not the important issue. The issue is whether the gesture respected her request for space. When someone asks for space, the most meaningful response you can give them is the space they asked for without trying to influence the outcome. That means no more flowers, gifts, letters, surprise visits, or messages through family members. It also means not looking for indirect ways to find out what she is thinking. You have already communicated that you care. She knows you want a future with her. She knows you’re unhappy with the current uncertainty. You do not need to keep proving it. If you want her to believe you understand her boundaries, your behavior now must demonstrate that understanding.

You object to her description of you as insecure because you consider yourself confident in other areas of life. You may be a confident professional, capable of making decisions, taking risks, and handling responsibilities, yet you can still feel insecure in a romantic relationship where the other person has not clarified her intentions. That does not make you weak; it makes you human. Uncertainty can produce anxiety even in people who are otherwise self-assured. When a relationship has no clear label, no agreed-upon expectations, and no mutually established direction, it is natural to wonder what it means. You are not unreasonable for wanting to know whether you are building toward a committed partnership. But there’s a difference between feeling insecure because a situation is uncertain and responding to that insecurity by trying to force certainty.

You seem to have become increasingly anxious about losing her, to which you responded by moving the relationship forward with the photo album, the promise ring, the parental blessing, and then the flowers. Each action may have been intended to secure the future you hoped for. But from her perspective, the relationship was moving faster than she was prepared to go. The more she pulled back, the more you tried to close the distance. And the more you tried to close the distance, the more she felt the need to pull back. This is a painful cycle, and it can happen even when neither person intends to hurt the other. Your task now is to recognize the cycle and stop participating in it. You must learn to tolerate the discomfort of not knowing your relationship status without attempting to control the other person’s decision.

You have been dating for 11 months. You have invested time, energy, and hope. You have introduced the idea of a future together, and that you are ready to move toward a committed relationship. Is it reasonable to want clarity after 11 months? Yes. You are entitled to want a relationship that has a future. You are entitled to want a partner who is ready to commit. You are entitled to decide that an undefined arrangement is no longer right for you. But there’s a crucial distinction between asking for clarity and demanding commitment. You cannot insist that she be ready because you’ve been dating for 11 months.

The time you have invested in her does not create an obligation for her to advance the relationship. Nor does it mean that she must agree to become your girlfriend or future wife. At the same time, her recovery does not obligate you to wait indefinitely. You are not required to suspend your emotional life until she completes a certain number of steps. You are not required to remain in an undefined relationship because she is a good person who has experienced hardship. You can care about her deeply and still recognize that your needs are not being met. This is where maturity becomes essential. You are simply not in the same place.

You mentioned that her parents love you and her mother has encouraged her not to let you go. I can understand why this gives you hope. When a woman’s parents welcome a man into the family and speak positively about him, it can feel like a meaningful endorsement of a future together. Their approval is certainly encouraging. But it is not decisive. Her mother may believe that you are an excellent match. She may sincerely worry that her daughter could lose a good man. She may appreciate the patience and stability you have demonstrated. But her daughter is the person who must decide whether she’s ready to enter a relationship with you. It’s especially important that you do not use parental approval as leverage, whether intentionally or unintentionally. Do not involve her parents in further discussions about rings, blessings, marriage, or the future unless she herself has welcomed their involvement.

Her relationship with her parents is separate from her relationship with you. Given the history you described, it’s possible that maintaining control over decisions involving her family is particularly important to her. The healthiest thing you can do is to step away from that triangle and allow the two of you to communicate directly if and when she’s ready.

Here is my advice: STOP chasing her. A healthy relationship requires two people who can express what they want, respect each other’s boundaries, and make decisions freely. Love is not a transaction. You may be a wonderful man and still not be the right partner for her at this stage of her life. She may be a wonderful woman and still not be able to offer you the relationship you want. Both things can be true. You cannot make someone ready for love. You can only decide whether the love being offered to you is one you can live with. And sometimes, the most difficult part of loving someone is accepting that you cannot determine the ending. May you have the wisdom to respect her journey, the courage to recognize your own needs, and the clarity to distinguish between a relationship worth nurturing and one you are trying to hold together by yourself. 

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at [email protected].