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Should I date this guy I like?

Ask the Experts: Solve your life dilemmas with expert advice from Maura O’Neill

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Don’t let past experiences inhibit you.

Don’t let past experiences inhibit you.

Don’t let past experiences inhibit you.

Dear Maura: When I get close to starting a relationship I instinctively step back because I know I’m going to get hurt. But I want this to change.

Recently I’ve got comfortable with a man I meet in a restaurant where I have my lunch. We both go there most days and have got chatting. He’s lovely, quiet and a bit shy. We’ve something in common as I’m very much a loner because of my shyness.

He’s often hinted about having more time to talk because we’re always rushing back to work, but I don’t let him say more than that because it’s so perfect now. I’m afraid if we have a date everything will change.

A bad relationship in my late twenties has left its scars. I’m now 32. I don’t want to lose this man, but my past has me doubting myself and I often think what if we did go out and it was a disaster.

There goes our chats at lunch as well. The other thing is I know that he will ask me out sooner or later and I need to be absolutely sure of my answer.

I want it to be ‘yes’ but as soon as I agree to go out with him, I know I’ll agonise about it. So, do I take a chance, push through my discomfort and hope for the best or stay safe and leave it as it is?

Answer: You know you can’t let this opportunity go by. I sense in your letter that you want to take a chance on this man. Most importantly you feel that if you let this potential relationship pass you by, you will be back to square one on your journey from that toxic situation in your late twenties.

In my opinion, you are drawn to this person because you are quite alike, have similar personalities and this gives you confidence. Another positive is you have managed to get closer with your lunch time chats.

The groundwork has been laid and that means no awkwardness. All you need to do now is say yes.

Dad isn’t keen on my new boyfriend

Dear Maura: My 89-year-old father is afraid my boyfriend will take over our house. I’m 49 and this is my first serious relationship.

He has his own place and I live with dad. Ever since I started seeing this man, dad is concerned about him moving in with us. But I would never do that.

It would be awkward, sleeping together with my elderly father in the house. But I can’t convince him and it’s making things difficult because I don’t feel comfortable having my boyfriend over to ours because of my dad’s attitude.

I would like to have my boyfriend stay every now and then, but dad doesn’t go away. So, it’s me going to my partner’s place most of the time.

I’m annoyed with dad, but I can’t say much. It’s his house and he’s 89 so I don’t want to be annoying him.
Answer: This relationship has come as a shock to your dad. It’s been just the two of you for so long.

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He needs reassurance that you will always be around for him and that’s at the root of his apparent negative attitude towards your boyfriend.

It may be awkward but talk to him. Tell him that you will always respect the fact that it is his home, and you won’t do anything to make him feel uncomfortable.

Email your problems to

  • Dr Angela Brokmann dr.angela@sundayworld.com
  • Maura O’Neill maura.oneill@sundayworld.com

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