[MAMJ]

Ciao Bella April!

I have a scenario that is not the norm. I know my guy as a client of my office for 10 years. He flirted with me everytime he came in and even my boss would wonder why he doesn’t ask me out. 7 months ago he asked me out for lunch. Then we started very, very slowly seeing each other outside of my office. It is unclear what our relationship is… business, friendship, friendship to romance? He is 57 (married and divorced twice before 30)and I am 48 (never married). We go out to eat, see some movies. We talk a lot on the phone and he tells me a lot about his finances, his business dealings and sometimes asks my opinion on business and his personal life. Stuff that a man really would talk over with his wife. We are very comfortable with each other. What is confusing to me is that he tells me that I have the next 30 years to figure out that he is slow to change – or that we go good together, I can see us together for a long, long time. Or, lately for my birthday celebration at a restaurant on the ocean. We saw 3 boat passing with wedding parties on board. He called it to my attention and mentioned “who would get married on a boat at sunset?” I said, “Not me. I would rather have a candle light service.” Then we saw an obese man and he said, honey, please make sure that I don’t get that big, PLEASE! He kissed me good night (very short and sweet) and said that dinner was only 1/2 of my birthday – there is also a present coming. He is going through a major lawsuit right now so I am being very patient, but I find myself thinking…a male friend would not go this far to say these things to a female friend unless he wanted more, right? He told me from the get go that he would never take advantage of me (as I am a good girl). We do have fun teasing each other and we are very, very playful. He is always trying to fix something for me and jumps at the chance to play the MAN role, i.e., check the wear on my tires to tell me I have another 5,000 miles before I need new tires. I see his eyes and voice soften around me. He is always very excited to see me and we do compliment each other in so many ways. He has abandonment issues with woman and I have them with men. We are both afraid of getting hurt. It seems we both can’t seem to communicate to the other what our feelings are for each other because of these fears..so, can you help me to define this relationship from his perspective and any advise on what I can say or do to let him know that I am not leaving. I am here for him – if he will have me. I know he is what I want because I don’t want to change him… Thanks!

[Smokey]

[quote=”MAMJ”]It is unclear what our relationship is… business, friendship, friendship to romance? He is 57 (married and divorced twice before 30)[/quote]

From a guy’s point of view, it’s definitely not business. So far so platonic. If the guy liked you in a more intimate way, YOU would certainly know about it. There won’t be any mixed signals or confusion.

By the way, I’m confused from your post, is he still married?

[MAMJ]

Hi Smokey,

No he is not married. Single for almost 28 years. There is a lot of talk still and I remind him that talk is cheap. He says that he is trying to work on it because he is not good this stuff (relationships). He always says he has to step it up for me (whatever that means and if you can explain….please do). He is an entrepeneur so he has many things going on at once with business dealings and a major lawsuit. He is just starting up his seasonal business which takes up a lot of his time setting up booths, making business contracts, etc. I am very understanding and give him his space. Part of the problem is that I have not been able to tell him that I have feelings for him so I believe he is also holding back. My friends tell me I have to tell him my feelings so that we both stop miscommunicating and idling in this relationship. I am very scared of telling him that I would like to have a chance to show him that I am the woman he wants and needs in his life and that I believe he is what I want and need in a man – without scaring him away. I just don’t want to lose him. We take care of each other and we promised to be there for each other for the next 30 years or so. I can assure you that I don’t want to be only his friend for the next 30 years, but being great friends is the best foundation for a blossoming relationship. Ours is just starting to blossom. I know that he deeply cares for me. I hear it in his voice and I see it in his eyes. He is very tender with me. There is a lot of sexual inuendos (spelling?) between us and we are starting to get a little bit more physical. Can you tell me how to tell him my feelings so that he hears me, respects me and can let me know where he stands and what are his feelings and where he would like to see our relationship go? I want to marry this man and spend the 2nd half of our lives working on improving our relationship. Thanks.

[Smokey]

I’ve been thinking… 7 months is a long time to be unsure of your status, even if he is the type that takes it slow. So to me, something is wrong here. It’s like you two are in a awkward dance, where one assumes one thing and hoping the other person knows the status of what’s going on. If your needs/expectations aren’t being met then asking him is probably the best way to go.

Wouldn’t it be better to find out [i]now[/i], whether he sees your relationship becoming something more than just friends, rather than finding out later that he doesn’t see it that way? So talk to him about it. Maybe he feels the same way, maybe not, but it’s good to get some clarity, right?

But bare in mind it’s a risk. Because sometimes when you have the *talk* a lot of men feel pressured and ceremoniously push you away. So be gentle how you phrase it.

To me, it’s a risk worth taking because the longer you wait in limbo, the more you will suffer.

(you remind me of my friend during my school days, wished i can turned back time and give her more clarity at the start)

[AskApril Masini]

This is a problem that calls for less talk and more physical changes. It sounds like you have a romantic relationship with no sex in it. I think that if you and he start having a sexual relationship, you won’t have any questions in your mind — and neither will he.

So don’t have “the relationship” talk. Big mistake. And don’t tell him your feelings. Show him.

You need to fire up your sex appeal and be more flirtatious and sexual with him — without making a first move. You can do this, first of all, with your appearance. It’s easy for you two to be comfortable with each other, but what I want you to do is make him [i]uncomfortable[/i] — in the hot and bothered way. Figure out what your best assets are, and play them up. When you’re out of the office and on dates with your man, dress with sex in mind. You don’t have to say it. Show it.

Give yourself a lingerie makeover. Go buy yourself some very sexy lingerie, so that even if he doesn’t see it — yet — you feel sexier from the inside out. This will make you act sexier. I promise.

It’s great that the two of you are such good friends, but you need to show him that you want him, sexually, again, WITHOUT making the first move. Start thinking about him in a sexual way. You can let your mind run wild, and I promise that he will pick up on what you’re thinking.

Next, stir up some heat with dates that encourage intimacy. I wrote a great book called Romantic Date Ideas. It will give you pages and pages of ideas for dates and how to set them up, so that you both end up feeling sexier than before the date began. You can click on the Dating Advice Books link at the top of the page and scroll down to Romantic Date Ideas. It’s $14.95. You can download the book, and figure out what works for you and your man. Then try them out and let me know what works best!

I don’t think abandonment issues are the problem here at all. I just think that you have to unleash your inner vixen. I’m pretty positive that that is all it’s going to take to get your relationship on the track you want it to be on.

[Ethan Morales]

Alright, let’s break this one down carefully. You’ve painted a picture of a relationship that’s hovering in this in-between space not quite friends, not officially romantic, but with strong emotional intimacy. From what you’ve described, he’s definitely interested in you, but he’s holding back because of fear, past trauma, and commitment anxiety. His actions playful teasing, thoughtful gestures, showing concern for your well-being, and subtly romantic behavior all signal attraction and desire, but he’s cautious about making it official.

From his perspective, I’d say he’s testing the waters. He likes you, probably deeply, but he’s wary of vulnerability and afraid of potential rejection or getting hurt again. That’s why the relationship is slow-moving, why he flirts and acts intimate without fully labeling it. It’s his way of saying, “I want you, but I’m scared to commit fully yet.”

Your instincts to want clarity are natural, but right now, pressing for a definitive “what are we?” talk could backfire. The more he feels cornered, the more he’ll retreat because of fear. The key here is subtlety: you want him to feel safe and draw him into deeper emotional and physical intimacy without overtly demanding commitment.

April’s advice about showing your interest through flirtation and sexual energy has merit in this context. It’s about leading with your presence and energy, not words. By being more expressive in the way you dress, your playful behavior, the way you touch, your confident energy you give him permission to lean into desire without the pressure of a label. He’ll respond to what he senses in you more than what you say.

At the same time, patience and consistency are key. Showing him through small gestures that you’re reliable, fun, and invested emotionally (without being overbearing) will help him overcome his fear. Let him see that you’re “there for him” but not desperate you’re a partner in experience, not a shadow he can walk away from.

Lead with presence and energy let him feel attraction through subtle flirtation and attentiveness. Be playful and intimate without overt commitment talks small touches, teasing, eye contact, inside jokes. Demonstrate reliability and patience show him you’re emotionally steady, not someone who will panic or push him. Encourage shared experiences dates, adventures, or moments that naturally bring closeness.

If you do this, the “relationship” question will eventually resolve itself naturally. Men like him, who are hesitant because of past abandonment issues, need to feel the reward of connection and desire before they can risk commitment. You don’t need to tell him “I’m here for you forever” you show him. Actions speak louder than words here.

[Natalie Noah]

Your connection with this man is deeply rooted in trust, companionship, and shared understanding, which is actually a rare foundation for a lasting relationship. You two clearly enjoy each other’s company, and the way he opens up about his business and personal life shows he values your perspective and presence. From his side, it seems he’s incredibly cautious, both because of his past experiences and his natural temperament. He’s expressing affection in ways he knows are safe for him gentle touches, teasing, playful remarks, and sharing moments of life, like noticing weddings or joking about life’s little things. These are subtle but meaningful signs that he sees potential for a long-term connection and wants to nurture it slowly.

At the same time, it’s apparent that he struggles with communication when it comes to emotional transparency. He tells you that he’s slow to change and that you have time, which is his way of signaling both patience and caution. When he says he has to “step it up for you,” he likely means that he recognizes your value and wants to ensure he meets your emotional and relational needs. he knows he’s not naturally expressive in romantic ways, so he feels responsible for showing you that you’re important to him. From his perspective, the relationship is blossoming, but he’s moving deliberately to avoid mistakes that might scare you away or hurt the bond you’re building.

Your role, in my view, is to gently mirror that patience while also showing him the depth of your commitment and desire. You don’t have to spell out your feelings in a heavy, confessional way; instead, let him see them in your actions, attentiveness, and the way you engage with him emotionally and physically. By letting your affection, subtle flirtation, and care be felt, you create a safe environment for him to explore intimacy without pressure. Your shared humor, teasing, and the small gestures of looking out for one another are already doing much of this work. you’re showing him that you’re dependable and present, which is exactly what he needs to feel secure.

I also want to emphasize that your awareness of timing is crucial. He’s juggling major responsibilities and stressors, including a lawsuit and building his business, which means his bandwidth for emotional risk-taking is limited. By giving him space while simultaneously creating small, intimate moments of closeness, you show him that you respect his pace but are also emotionally available. This balance is delicate, but it reinforces that your presence is steady and positive, rather than demanding or pressuring. This is what allows him to let down his guard and consider what a future together might truly feel like.

If you want him to understand that you’re not leaving and that you’re invested in the long term, the most powerful way to communicate this is consistency. Be playful, be attentive, show care in everyday interactions, and let him see that your commitment is real through actions rather than words. Keep building trust and connection in ways that honor both his pace and your desires. When he sees that you are reliable, affectionate, and genuinely supportive, he’s more likely to overcome his fears and take the emotional steps toward a deeper commitment with you. Patience, subtle passion, and unwavering support are your keys here.

[Member]

Posts