Should I Chase Someone Who Is Married? Help Me Love Doctor

Why not send former Kingston-resident Love Doctor your relationship queries? Use the form to submit your question(s).


I met a married woman over the festive season, who wears a wedding ring but we have never discussed her domestic situation.

We get on like a house on fire and flirt, but should I pursue her?

Benjamin, Kingston



Love Doctor’s Answer:

Love Doctor MontiIn some ways you are showing that you are a real man by thinking with your mind and considering the potential repercussions should you two strike up a relationship.

Many men would think below the equator and be selfish about this, because as soon as an attractive-looking lady flirts men can easily become putty in their hands.

It is wonderful that you two got along so well and flirted. Yet you should not forget that it was the season of goodwill and people tend to have a drink or two, so they can appear to be more flirtatious than they would usually be.

Just because she is married does not mean that her sexuality has vanished. She may well have been strongly attracted to you, even though she is in love with her husband. However, acting on her desires and urges is what becomes an issue.

The big question is whether you exchanged contact details to meet up again, or whether this was just a brief bit of flirting fun and she wanted to check out whether other men – apart from her husband – find her attractive.

If you do have her number, then before you contact her I suggest you do a little bit of detective work to find out about her marital status. She could be widowed, separated or divorced as quite often ladies like to keep their wedding band on as a feeling that they have been adored.

If you discover that she is happily married then you certainly should step back and even delete her details so that you are never tempted to contact her. Just because there was flirting could easily have been quite innocent, and we all need to know at some stage of a relationship that we still possess the ability to turn someone’s head.


Should she be available then of course you can chase her up with a message along the lines of “What sort of trouble are you getting into this weekend?” This should gauge some interest and a response.

Then you can make the brave step of actually calling her and having a chat. Meeting up is not particularly easy with this fourth wave of COVID-19 across the island, but you should keep in touch with her on a regular basis and show your caring side by ensuring that you message her in the mornings so that she knows you are thinking of her.

If she is interested in a long-term relationship then expect in your messages to receive kisses or heart emojis and to be referred to by such names such as baby, darling and honey.

I urge you to not become too dazzled by these and concentrate on being curious about her past relationships during your conversations. Show that you care by asking about her romantic life and history, from her first kiss to her biggest heartbreak. If you can show open communication and dollops of empathy then you will be in her good books. 

These chats offer you some of the telltale traits that most ladies find attractive in a man such as confidence, genuine friendship, kindness, mental compatibility and a sense of humour. If you can inject these aspects into your conversations then you are in pole position to get the romance running at full throttle.

Once she has trust and faith in you then it is likely that she will up the ante in the emotional stakes and show more intimacy by voicing her fears and insecurities, which could include any former marital issues.

Should she suddenly share an issue about her marriage, and begin to explain current cracks in her relationship then it is time to walk away rather than get dragged into a sticky situation. You need to avoid treading on treacherous terrain for moral reasons. 

Trust me, you do not want to be her knight in shining armour. If she is prepared to run away from him and into your arms then there is no reason why she will not repeat the same action with you. So watch out for phrases that she may drop such as “How come we didn’t meet before I made the mistake of getting married?” and “If only my husband was like you”.

Any relationship is going to be demanding – emotionally, financially, mentally and physically – and you will soon feel drained if you allow her to cheat on her husand with you, because at the end of the day you are most likely to simply be a shoulder to cry on.


All you can do is try to find out the true story and then plan accordingly.  

Click here for Guidance In Seeking A Soul Mate

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