Is he playing a game with her?

November 6, 2026 by No Comments

Hi Terry-

I love your book and love getting your regular emails. The advice you give is so real with no holes barred. Many relationship experts go on an on with a whole lot of psychological babble. I like the way you tell it like it is. I wonder can you give me some advice on this scenario:

I am separated about 2 1/2 years now. Shortly after I separated I met a doctor, randomly, one night in a bar and we hit it off. We started seeing each other regularly and he was very attentive, calling me up all the time, asking me out etc. He did all the chasing and I started to fall for him. About 3 months into our relationship he told me that his ex girlfriend had returned from Germany and would be working with him at the hospital he works at. I asked him did he want something to happen between them. He said he wasn’t sure if anything would happen but wanted to be upfront with me as he didn’t want me to get hurt. Anyway, to cut a long story short I ended things with him as I didn’t want to become like a Third Party standing on the side lines. That was in June 2009.

Since then, he sent me the odd text and we spoke on the phone a couple of times. Several times he ended the call saying “I’ll give you a shout” and then I wouldn’t hear from him for months. I bumped into one night in town in November 09 and we ended up going for drinks together and he asked me out for dinner. We went to dinner in December and had a great night out and then I never heard from his again (only got a poxy Happy Xmas text on Christmas Eve). At that stage I was seeing someone else so it didn’t bother me.

I’ve been single again for 6 months and about a month ago I sent him a text to see how he was. He rang me straight away and sounded really happy to hear from me and asked me to meet him for dinner. So, on the 1st Octoer we went for dinner and drinks in town and had a super night, great fun, lots of flirting and smooching. He was heading to Peru for two weeks on holidays the following day but said he would call me when he got back. I went on a family holiday to LA with my kids on 21 October so he never got in contact before I went away. Also, when I was away in the States (I’m from Ireland) my phone didnt work for the whole time I was away so I didnt know whether he tried to make contact or not.

Again, to cut a long story short…..here’s my dilemma. I sent him a text the day after I got back and said that I was back from LA and if he tried to make contact my phone wasn’t working in the States. He called me straight back (as he always does) and we chatted about both our holidays but he never mentioned whether he had tried to make contact or not and I never directly asked him either.

Anyway, he asked me to meet up with him again and we arranged for this Saturday coming. He was headed to Portugal for a week’s golfing and I said that I would book a restaurant seeing as he would be away. That was a week ago and he is due back this Saturday and our date is for Saturday night, however, he has not made any contact since. He has not even text me to see where we are meeting up on Saturday. I reckon that he won’t be in touch until his flight lands on Saturday afternoon and we’re supposed to be going out that night. This whole thing just doesnt feel good to me anymore. Its feels like he is playing a game with me and wants to see how far I will chase him. Should I send him a text to tell him where I’ve booked for dinner out of courtesy or should I wait until he does it even if its late Saturday afternoon.

I feel that if he was really interested in me he would have been in touch before now and it’s a total lack of respect for me if he doesnt make contact before Saturday. My gut instinct is to cancel the dinner reservation if he doesnt make contact before Saturday. He doesn’t deserve to see me if he is not going to make even one small gesture. Am I overreacting and expecting too much too soon?

What would you do?

If you have the time to give me any insight at all it would be great. Thanks so much. Your emails and book have been a great source of inspiration for me.

Kind regards

-Wondering in Dublin

Dear Wondering:

You write, “This whole thing just doesn’t feel good to me anymore.”

Trust your instincts. There’s no need to text this guy or initiate any sort of communication. He’s not working very hard to see you (although he may truly like you), and who needs that?

You want a guy who makes it plain that he cares at least enough about you as you care about him.

It’s sticky when you feel this all this mutual attraction with somebody, and then they inexplicably don’t follow through. It’s easy to tell yourself you’re not being patient or, worse, that you’re overreacting.

But, look at it this way: What if you met a woman at a book signing, and you hit it off? You became instant friends. You went out for lunch, had a great time, and found you had even more things in common. She seemed to be as interested in this new friendship as you did.

You agreed to get together the following week and see a show. She said she’d call. She didn’t.

Would you think you were being less than patient when she didn’t call? Wouldn’t you have worried that you were overreacting?

I don’t think so.

What I’d think in that situation (because it has happened, you know) is that she was one of those people who makes a great first or second impression but is ultimately probably not worth my time — unless she proved otherwise — by apologizing, by keeping her word from then on, etc.

In other words, don’t accept behavior from a man that you wouldn’t accept from a woman.

If he does happen to come around, great. But let him come around and be very slow to accept another offer from him. Make him prove to you he’s even worth your time.

In the meantime, keep busy, have fun, and see other people. This is your life we’re talking about.

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