Would Dating An Older Woman Be A Waste Of Time? – Help Me Love Doctor

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


I’m in my 40s and never dated anyone older than me, but now I’ve met someone who I like and want to ask out. I worry though, would I be wasting my time?


I work in sales and definitely clicked with this single sexy lady, who is about 10 years older than me. We’ve met five times professionally and now I want to suggest going out on a date, what should I do?

Wilson – St Elizabeth 

Love Doctor’s Answer

There is no age barrier to true love, and if you feel that there is a genuine connection between the two of you then why not ask her out?

Just because she is older than your usual dates doesn’t mean she is not seeking fun. While ladies 10 years younger or more than you may have fancied going to dancehalls on Fridays and Saturdays, an older lady will already knows what she wants to do to enjoy life.

Don’t be scared to ask this lady out as she is likely to accept your invitation to arrange a date. Her face is likely to light up when she tells her galpals that you have picked her over younger ladies.

If you can exude confidence and are able to impress her with a choice of things to do on a potential date, then this will add more excitement to your first rendezvous.

An older lady, who boasts life experience, will be more mature emotionally. She will probably be seeking a genuine man to make her feel sexier than she already is, and to find a person to share life experiences with together will be exactly what she desires.


Whatever you do try and be assertive while also being a true gent. Obviously don’t bring up the age difference, let her do that, and if you do start courting then don’t change too much for her otherwise you will be out of your comfort zone.

If you ensure that all of your interactions can show a real interest in who she is, and are able to keep the conversation flowing, there is no reason why you two cannot get along like a house on fire.

One of the common drawbacks with dating an older lady is her baggage that she brings to the relationship, which could even include her being a grandmother. Do consider how you would feel stepping into that scenario and whether you could cope before you even entertain asking her out on a date.

Remember that the majority of single men in her age bracket are probably not in the physical shape that she desires, so as long as you are reasonably attractive and fit then it is unlikely she will turn down a date with you.

What she will be wary of is of men who are after one thing, as well as those who are already financially broken and/or emotionally destroyed following a divorce. If you are in either of these categories then I would be apprehensive of asking her out on a date, as it could all end in tears.

My advice is to visualise what she will look like in five years, look at other ladies who are now that age and work whether you find them attractive. This lady may excite you now, but do you think in five years will you still feel passionate towards her? It is best to be realistic now rather than waste each other’s time.

Experienced women are a definite asset to a man regardless of age as they tend to appreciate that life is better when you are in a romantic relationship. If you can make her feel  special, and can show over time that you can be a solid partnership, then unquestionably she will be a true asset for a happy and fulfilling life.

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